


Agony

by alpacamybags



Category: Supernatural
Genre: Angst, Castiel and Dean Winchester and Sam Winchester are Jack Kline's Parents, Dadstiel angst, Found Family, Gen, Hurt Castiel (Supernatural), Hurt Dean Winchester, Hurt Jack Kline, Hurt Sam Winchester, Hurt/Comfort, Protective Castiel (Supernatural), Protective Sam Winchester, Some Fluff, Team Free Will 2.0 (Supernatural), Team as Family, Whump, Whumptober 2020, Yippee, and then 35 percent sam, but everyone will get whumped don't worry, everybody gets whumped, like a lot of it, strap in lads this is gonna be a long angsty ride, this is about 50 percent cas and jack
Language: English
Status: Completed
Published: 2020-10-01
Updated: 2020-10-30
Packaged: 2021-03-08 03:21:38
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 31
Words: 33,618
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26748694
Author URL: https://archiveofourown.org/users/alpacamybags/pseuds/alpacamybags
Summary: Torturing Team Free Will 2.0 and assorted guest stars with the Whumptober 2020 prompts.
Relationships: Bobby Singer & Dean Winchester & Sam Winchester, Castiel & Dean Winchester & Sam Winchester, Castiel & Jack Kline, Castiel & Jack Kline & Dean Winchester & Sam Winchester, Castiel & Kelly Kline (Supernatural), Dean Winchester & Sam Winchester, Jack Kline & Sam Winchester, Jessica Moore/Sam Winchester
Comments: 91
Kudos: 150





	1. Let's Hang Out Sometime

**Author's Note:**

> Happy October everyone! I've never attempted anything like this before, so let's see how it goes.  
> As these are basically torture prompts, some material will likely be triggering. So instead of having 50 miles of tags, I'll put warnings in the beginnings of chapters for anything beyond canon-typical violence and angst. Please be careful, and stay safe while reading. T-rating is for language, canon-typical violence, and dark themes.

**Summary for the Chapter:**

> Day 1: Hanging  
> Whumpee: Dean  
> Set Season 1-ish for the nostalgia

Sam, for whatever reason, was always the one who got strangled. Dean would usually swoop in at the last minute, make sure Sam wasn’t in any actual danger, and then they’d saunter off after a job well done. 

So why was Dean the one with the noose around his neck? 

Not that he’d ever wish this on Sam. God, no. But here he was, spots dancing in his eyes, hands trying to pull the rope away best as he could, toes scrabbling for any bit of purchase on the ground. 

It was probably some kind of twisted karma from all the times he’d seen Sam get choked. Now the universe needed the other Winchester to have a sore throat for a week. 

He was starting to think he wouldn’t have to worry about that, though. 

The ghost had been hanged when this little town was just a good ol’ cowboy stop on the western frontier, and after it killed a few kids who’d been dumb enough to come to the haunted house- the _historic_ town hall- it’d made the papers. In come Winchesters, bye-bye goes the ghost. 

In theory. 

Instead, the son of a bitch had gotten Dean strung up on the very tree he’d died on, using some freak-ass ghostly manifest power to get him there. It wasn’t even a real noose, though it sure felt like one. 

Thankfully, there was a growth of roots underfoot he could sort of stand on, and though he wasn’t taller than Sam, Dean was still taller than the man who’d died here. 

Taking another gasping breath as the noose tightened, Dean felt his body relax, numbness spreading through the muscles. Nope, not good. Bad. Where was Sam? Where was _he_? What was…

The next thing he knew, Dean hit the ground, coughing around ragged gasps of refreshing, foul-smelling oxygen. The good news was that it meant he’d live. The bad news was that now his neck _hurt_. 

“Dean!” He felt Sam crashing to the ground beside him, knees colliding with Dean’s elbow. 

“Jesus, Sammy, can’t a guy breathe in peace?” His voice was definitely not a faint rasp. Not at all. “Did you get him?”

Sam huffed a half-laugh, one that meant he was annoyed but more relieved than anything else. 

“Yeah, finally found the bones. You okay?” 

Dean sat up, ignoring the way the world spun around him. He’d be damned if he wasn’t driving them out of here. “Yeah, yeah. Thought gettin’ strangled was your hobby, not mine.”

Sam’s eye roll was befitting of a teenager. “Whatever, jerk. Let’s go.”

Sam helped him up with a hand on his arm, which Dean promptly shrugged off upon standing. No need to get all chick-flick-y now. 

“‘Kay, bitch. Let’s go. Another successful day in the life.” 

“It wasn’t successful, Dean. You got strangled.”

“I _almost_ got strangled. And we still ganked the ghost.”

“You were hanging from a tree with a magic noose. That’s practically the definition for strangulation.” 

“Uh huh. Know that ‘cause you used to read the dictionary before bed?” 

They bickered the whole walk to the car. It most definitely did not hurt Dean’s throat.

**Notes for the Chapter:**

> So this one didn't end up being duper dark. Oh, well- that's coming. No need to worry :)  
> See y'all tomorrow!


	2. In the Hands of the Enemy

**Summary for the Chapter:**

> Day 2: Kidnapped  
> Whumpee(s): Jack, Maggie  
> Warning for some creeping on teenagers (or one-year-olds who look twenty)  
> Set between seasons 13 and 14

Jack was really beginning to hate not having his powers. He’d been out with Maggie going grocery shopping for the Bunker, since Sam and Castiel were busy and the majority of the new hunters were still settling in. Some had already taken cases, and so Maggie and Jack, as the resident young people, were tasked with grocery duty. 

What they hadn’t been counting on was two burly men in masks walking in, pointing a gun at the cashier and shouting for everyone else in the store to get down on the floor. 

Jack had never experienced a robbery before. He’d seen the aftermath last year in the ghoul cowboy case, but that hadn’t gone well. At all. 

Maybe it was a good thing he didn’t have powers right now. The bad news was that they didn’t have weapons beyond small knives, and he was sure they wouldn’t be much use. What was that saying? Never bring a knife to a gunfight?

Oops. 

So Jack and Maggie knelt down, watching as the terrified teenager behind the counter started emptying the cash register. There was nothing they could do.

One of the men looked around while his partner kept a gun trained on the cashier. His eyes settled on Maggie, and he gestured with his gun. “You, girl, up. You’re coming with us.” 

Maggie’s eyes darted to the side to meet Jack’s, and she started to stand up. 

“You too, boy.” 

Jack slowly climbed to his feet, hands raised non-threateningly. If only he still had his powers, he might have had enough control to knock the guns away. As it was, he and Maggie were paraded to a white van, their wrists duct taped behind them. They were shoved inside, but not before the men found their pocket knives and phones. 

“Think we should call someone on one of these phones for ransom?” One of them, the blond, said as they slid into the front seats and started speeding off. 

The other one scoffed. “They don’t look like rich kids. They’re just insurance to make sure no one tries anything. We can dump them somewhere later. Or keep ‘em around a while. They look like fun.” 

The blond looked back at Jack and Maggie, their faces carefully blank. They’d been through worse. Jack kept reminding himself of that. 

“I’m calling someone anyway, just for kicks. Ain’t like there’s anything they can do about it. Oh, let’s check the speed dial. Maybe mommy and daddy can get all worried and tell us their credit card numbers.”

He clicked the speed dial on Jack’s phone, turning it to speaker. Castiel’s voice came through the other side. 

“Jack? Is everything alright?” 

Their captors grinned at each other, masks off by now. Jack had never seen them before, and he was sure they were human. They really didn’t have a clue what they were getting into. 

“Yeah, if you want the kids back, you’re gonna have to wire us all the money you got, and meet our demands exactly. Otherwise, I think we’ll put a bullet in their pretty little heads.”

The change in Castiel’s voice was immediate. “Who are you. And where. Is. Jack.” 

The blond man’s grin fell. Maggie and Jack exchanged a look. Sam and Castiel would come to get them soon. Their phones had trackers, and these men hadn’t yet disabled them. 

“Who I am isn’t important. But if you want to see them again, you'll do what I say.”

“If you hurt a hair on their heads, I will make sure you do not live to see another day when I find you. And I _will_ find you,” Castiel growled. 

“Oh, you don’t want me to hurt them?” 

A hand reached back blindly, and it clasped in Jack’s shirt. He yanked, and Jack’s head collided with the metal wall of the van. He yelped, and then the man pushed him back. Maggie scooted over to him, glaring at their captors as Jack tried to regain some composure. 

The silence across the phone was ice cold. When he spoke again, Castiel’s voice was low and dangerous. “I will give you one more chance to tell me where you have them. If you tell me now, I might just spare your life.”

“Hmm. Yeah, no dice. I think I’ll just have some fun and drop their bodies in a ditch somewhere. Been nice talkin’ to ya.” 

He hung up, throwing Jack and Maggie’s phones out the window. 

“Sit tight, kiddos. It won’t be long till we stop.”

Maggie bumped shoulders with Jack, asking with her eyes if he was alright. Jack nodded, checking to make sure their captors were focused on the road before turning to Maggie and mouthing, “pray.” 

She nodded, and they both closed their eyes. 

_Castiel._

\-------------------------------------------------------------------------------------------------------

They stopped driving after a few hours, pulling off into the woods where an old, torn up house stood. Jack’s legs were losing feeling, his wrists were cramping, and his head was still throbbing. Maggie was in a similar situation next to him, arm still pressed to his. 

Jack was beginning to worry about what would happen if Castiel and Sam couldn’t find them, or took too long. Some of the looks and comments the men tossed towards them made Maggie blanch, but Jack didn’t really understand them. Despite all he’d been through, he was still only one year old. 

He sent another prayer to Cas, to say that they’d stopped and were alright. Just hoping the angel could hone in on their location, Jack allowed himself to get dragged out of the van. 

The cabin was run down, with moldy floors and rotting rafters. Their captors sat and made themselves some food, Maggie and Jack left to their own devices in the corner. Their knives were with the guns on the corner of the table. 

“Should we run?” Jack whispered. 

Maggie shook her head. “They can get to the guns easy. We shouldn’t risk it.” 

So they sat. Eventually, the driver came over, looking them up and down. Jack fought the urge to squirm, praying to Castiel again. 

The driver knelt down, running a finger across Jack’s chin and jaw. Jack tried to stare him down, angry and confident, like one of his fathers would. It seemed to have the opposite effect. 

“I think I like you, boy. And you’re so good and quiet too.” 

“Get off of him,” Maggie snapped. 

“Maggie, it’s okay,” Jack said, as the man reared back. 

“The hell did you say to me, bitch?” 

Fortunately, he didn’t get to do anything else, since the roar of the impala sounded from outside. Relief flooded through Jack, intense and immediate. 

The door flew open, revealing Sam and Castiel, both looking more angry than Jack thought he’d even seen them before. If he didn’t know them, he would be scared of them. 

“Get away from them,” Sam snarled, raising his gun. Castiel had a gun too. It was an odd sight. 

“Why should I?” The driver had a knife, seemingly from nowhere, and he pressed it to Jack’s throat. The other man also had a gun pointed to the door. 

Castiel stepped forward, eyes flashing blue. “Step away. I won’t ask again.” 

The gun and knife were away faster than Jack would have thought possible. Castiel herded them out the back of the cabin, while Sam hurried over to Jack and Maggie. 

“Are you hurt? What did they do?” 

Sam pulled the tape off of Maggie’s wrists first, then Jack’s. He helped them to their feet, wrapping an arm around each of them, quick and desperate. 

“We’re fine,” Maggie whispered, her voice wavering slightly. “They didn’t do much, just threats.” 

Sam nodded, features relaxing as he took them in. “Jack? You okay?”

Jack nodded, feeling a sudden wave of exhaustion. Castiel rushed back inside, the stony expression from earlier replaced with open worry. He pulled Jack to him as soon as he was in reach, and Jack sank into the embrace gratefully. 

“You’re alright?” Castiel pulled back, looking him up and down for injuries. 

“I’m okay,” Jack whispered. It was all he could seem to muster. 

Castiel didn’t look convinced, but simply pressed his fingers gently to Jack’s forehead. The wave of grace cleared his head somewhat, and Castiel moved forward to heal Maggie as well, asking her if she was alright. 

Sam’s hand descended to Jack’s shoulder, warm and heavy. Jack leaned into the touch. 

“You sure you’re okay?” Sam asked. 

Jack watched as a faint light shone underneath Maggie’s skin, the flare of Castiel’s grace soft and warm. 

“I think so,” he said. “Or I will be. I just really want to go home.” 

Castiel and Maggie faced them again, and Sam squeezed Jack’s shoulder. 

“Okay. Let’s go home.”

**Notes for the Chapter:**

> So it turns out whumping Jack is like- scary easy for me? Which I then feel very bad about, because he's my sweet cinnamon baby and the show puts him through enough. I think Jack might actually be the one who will get hurt the worst in these chapters. Or Sam. I guess I'll see how it turns out, aha. 
> 
> Anyway, thanks for reading! Reviews are much appreciated.


	3. My Way or the Highway

**Summary for the Chapter:**

> Day 3: Held at Gunpoint  
> Whumpee: Sam  
> Set pre-series, Stanford Era

“Don’t move!”

Sam heard the shout from behind him and sighed, lifting up his hands and turning around. There was a guy there, a shaky gun pointed right at him. Was he honestly being mugged? What about Sam’s ratty backpack and second-hand clothes screamed anything other than “broke college student?”

“Okay,” Sam said, voice steady. He really thought he’d been done with the constant mortal peril. “I’m not moving. You wanna put the gun down?” 

“You do what I say, buddy. I’m the one with the gun.”

_Yeah, no shit, Sherlock._

Sam resisted the urge to roll his eyes. This guy wasn’t that muscular. Sam could probably take him. Or maybe not. Neither Sam nor Dean looked like they’d be very strong, but they’d been re-killing the dead for a decade. 

_Shit. Don’t think about Dean._

“Look, man, I don’t have any money. I don’t know what you want me to do.” 

“Just gimme your wallet.” 

Sam paused. Really? At least his mugger was an amateur. 

“You want an empty wallet?”

“You gotta have something valuable in there. Don’t make me shoot you.” 

“You won’t.” That was a new voice, from behind the mugger. It was a girl, blond waves cascading around her face. Sam thought he’d seen her before, around campus. 

She held up a cell phone, dangling it between her fingers and swinging it from side to side. 

“I’ve called the police, so you can either stay here and get arrested, or drop the gun and leave. Your choice.” 

She took a step into the light, making her face glow and her eyes light up. She looked like an angel. Sam thought he might be in love. 

The mugger didn’t drop the gun, but he did turn tail and run. Sam felt his muscles relaxing again, and he turned to face his savior. 

“You okay?” she asked. 

“Yeah, thanks. I’m Sam,” he said, trying not to stare too obviously. She was just so… _beautiful_. 

“I’m Jess,” she replied, extending a hand. Sam took it, a memory flashing in his head. 

“We met!” He blurted. She looked at him like he was insane, lips quirked up. 

“Yeah, pretty sure that’s the point of the handshake.”

Sam blushed furiously. “No, no. I mean, we’ve met before. At Luis’s party, the other weekend. Brady introduced us.” 

Recognition alighted on her face. “Oh, yeah, you’re right! Not that I really, you know, remember much from then,” she said, somewhat sheepishly. 

Sam rubbed the back of his neck. “Yeah, I don’t think anyone does.” 

The alcohol had flown freely at that party. There’d definitely been a keg, and Sam had rather stupidly smoked a joint. He thought it might have actually been oregano, since it didn’t do much, but he couldn’t be sure. 

The whole night was a blur. 

Now though, a star shone out of that blur. And her name was Jessica. 

And Jess laughed, now, soft and sweet. Like music. “You sure you’re okay, Sam? I mean it isn’t every day you get held at gunpoint.”

_It wasn’t exactly my first time._

“I’m fine, thanks. I don’t think that guy was actually gonna shoot.”

“Still.”

Sam smiled. He really, _really_ liked this girl. 

“Hey, can I, uh, walk you back to your dorm?” 

Jess smirked at him, eyes glinting. “That’s a little forward, don’t you think?” 

Sam blushed again. “No, no, that’s not what I-”

Jessica’s laugh was louder and freer this time. “Don’t worry, Sam. I’m kidding. Why don’t I walk you back to your dorm and see where it goes from there, okay? I did save your life, after all.” 

Jess grinned at him playfully and walked away, Sam staring like a dopey idiot before he got his feet to move again. 

Saved his life, she said. He really thought she had. 

In more ways than one.

**Notes for the Chapter:**

> Can't have Stanford Era without SamJess ;)  
> Thanks for reading!


	4. Running Out of Time

**Summary for the Chapter:**

> Day 4: Collapsed Building  
> Whumpee: Jack  
> Set early season 14, when Jack and Cas were hunting together. Don't remember what episodes it was, but Jack doesn't have powers and does have his soul.

The poltergeist in this apartment building was not stopping, in spite of Castiel and Jack’s best efforts. They were rushing the family that lived in the haunted apartment out the front door, having pulled the fire alarm so the others evacuated, but as Jack looked around outside he realized their young daughter was missing. As the father shouted for her, Jack barely glanced at Castiel before shouting “I’ll get her!” and dashing back into the house. He didn’t see the little girl run into her father’s arms from the crowd, and he couldn’t hear Castiel shouting for him over the din of the crowd and the roaring of the sirens. 

Jack made it back into the building, and was rounding the corner to the stairs when a crack sounded from above, and the ceiling caved in. 

\----------------

Castiel felt like the very ground had been pulled out from under him when the building creaked and collapsed. Jack was in there. _Jack was in there._

The local authorities had arrived, and they were holding the crowd back. The building was only two stories, but it was wide, and there were scores of people who had all evacuated. Castiel pushed to the forefront of the crowd, fully intent on running inside, not stopping until he had Jack safe and sound and in the car on the way home. Or wrapped in Castiel’s arms, where he could be sure Jack was whole and well. 

Two firefighters had him by the arms, and Castiel was so desperate he considered ripping his arms out of their grasps. He could easily do so, maybe even breaking their fragile wrists and elbows and shoulders in the process. But he wouldn’t hurt innocent humans, he couldn’t. So he attempted to use his words. 

“Please, my son is in there, I have to-”

“Sir, you have to stay back. It’s not safe.” 

Castiel took a deep, deep breath. He couldn’t just stay back. Not when Jack was in danger. 

He pushed through the firefighters, using just an inkling of his angelic strength, and ran into the smoke and dirt and particulates churned up by the building. 

\-------------

Jack was dazed, and his head was spinning. He opened his eyes, only for swirling dust to fall into them. He slammed them shut, trying to move his hand up to wipe at them, only to be met with searing pain. He cried out, realizing his arm was stuck under a slab of concrete. Another one had fallen over his hips, effectively pinning him to the ground. He was trapped. 

“Help!” He shouted, coughing through the dust. His voice was too quiet, too hoarse. No one would hear him. “Help! I’m stuck!” 

Jack’s voice broke, and his breath hitched on a sob. His instinct was to curl up into a ball, but he couldn’t move. He couldn’t feel his toes, and he was far too weak without his powers to even shift the beams and brick. He still pushed weakly at it with his free hand, but it was no use. 

He sat and cried trying desperately not to. Time spun around and away from him in a haze. His entire body felt fuzzy, like he was floating. Blood dripped down the side of his head, in a place he couldn’t reach to wipe it away. He didn’t even know if that’s what you were supposed to do with bleeding head wounds. Sam would know, Sam knew everything. 

Sam. Jack wanted so badly to be home right now, watching movies with Sam and Cas and Dean. He liked to see them smile and laugh, since they didn’t seem to do it that often. And then maybe he could persuade Castiel to tell him a story about Heaven before his human body made him fall asleep. He loved listening to Castiel’s stories of years and years ago. 

Another chunk of concrete crumbled off of the wall that was still standing beside him, landing on the beam over Jack’s legs. He screamed, the pain flashing white hot and jagged. 

And then he heard Castiel. “Jack!?” 

It was a frantic, desperate shout. Jack couldn’t see Castiel through the haze, though he lifted his head and squinted as hard as he could. 

“Cas!” He yelled back, loud as he could. He dissolved into another coughing fit. 

Castiel came into his field of vision, staggering across the concrete slabs and remnants of light fixtures that decorated the floor. Jack felt a new onslaught of tears at the sight. 

“Cas, help me, I-”

“Jack,” Castiel leant over, a hand on Jack’s cheek to examine his head for injuries. He frowned when he saw the blood dripping from near his right ear. 

“Oh, Jack,” Castiel said, looking him in the eyes. “It’s going to be alright. You’re going to be alright, but I have to move the beams before I can heal you, and it’s likely to hurt. Are you ready?” 

Jack forced a nod, taking in a shaky breath. He coughed again, and as Castiel pulled away, Jack instinctively grabbed his sleeve with his free hand. Castiel slowly removed it, squeezing it gently and settling it over Jack’s chest. 

“You’re very brave, Jack. You can do this.” 

Brave? Jack wasn’t brave. Sam and Dean were brave. Jack was trapped, and he’d just started crying. Like a child. No matter how much he tried not to be, he was still a useless, helpless child. 

In Castiel’s eyes he didn’t see that. Castiel said Jack was brave, and he believed it. So maybe Jack could believe it too. 

Castiel lifted the chunk of ceiling from his arm first, and Jack cried out, because somehow the pressure release hurt even more. 

“Don’t move your arm yet. Stay as still as possible,” Castiel instructed, moving to the beam across Jack’s hips. 

Taking off the second slab to fall didn’t hurt that much, but the beam itself was simultaneously a relief and a terror, as he could feel the blood start flowing freely in his legs again. Which meant he was starting to get feeling back, little thorns of pain that replaced the tingling numbness. 

But his father was kneeling next to him now, gentle fingers on his forehead and his arm, and the pain began to fade. When it was gone, Castiel pulled Jack into his arms. 

Jack was finally able to curl into a ball, with his head tucked under Castiel’s chin and his face buried in his chest. 

“You’re alright, you’re alright.” Castiel was repeating that phrase over and over, rocking them back and forth, and Jack couldn’t quite tell which one of them it was for. 

Castiel pulled back, eyes scanning over Jack’s face as his hands came up to his cheeks. 

“I’m incredibly proud of your selflessness, Jack. But you _have_ to be more careful. Promise me,” he said, and it came out strangled and desperate. 

Jack could see the worry in Castiel’s eyes and the lines of his face, could feel it in the way his hands kept moving, from Jack’s shoulders to head to neck, as if making sure he was still there. Jack had been so scared, alone under that beam, but he began to realize Castiel had been terrified too. _For_ Jack, because he loved him. It was nice to feel loved. 

“I promise.”

**Notes for the Chapter:**

> I just really love Dadstiel and his nougat son you guys.  
> Reviews are always appreciated!


	5. Where Do You Think You're Going?

**Summary for the Chapter:**

> Day 5: On the Run  
> Whumpee: Castiel  
> Set between 15x03 and 15x06. So, incredibly angsty, and he's rightfully mad at Sam and Dean, so if you don't like that I'd skip this chapter. It's not anti by any means, and certainly less bitter than I thought it would turn out to be, but just in case.

Castiel left the Bunker, and he didn’t look back. That didn’t mean it didn’t hurt. Because it did. But this hurt was buried low, deep within him. And hanging over it all was the loss of Jack. That… that hurt most of all. 

He didn’t think he’d ever heal. 

So he got in his truck and drove, no clear destination in mind. Even driving was hard, though. It brought too many memories. Sam and Dean were creatures of the American highways, after all, and the first time Castiel truly had with Jack was spent in the back of the Impala as the four of them drove to Dodge City. Their little family, built from scratch, layered with blood and tears in place of bricks. 

Oh, how it all fell down. 

Castiel pulled over in the first town he came to. He was still in Kansas, probably on the outskirts by now. He found a restaurant, resolutely not selecting a diner, and sat in the parking lot with his truck turned off. He’d always hated feeling purposeless, and that’s all he felt right now. Useless and aimless. 

He couldn’t even protect his son’s corpse. 

Castiel got out of the car and hurried into the restaurant, taking a seat in the bar area by himself. He ordered a burger, which he realized was a mistake as soon as it was set in front of him. Jack had loved burgers. Dean loved burgers. Sam even enjoyed them at times, especially if they came from more upscale places where the meat was less greasy. 

He left a generous amount of money on the table and left. It wasn’t as if he had to eat anyway. 

\-------

He learned that the city was called Goodland, and was somewhat near the western border of Kansas. Castiel decided he may as well stay for a few days. He went to the same restaurant for breakfast in the mornings. He didn’t really eat any other time, but he’d gotten used to at least having breakfast in the Bunker. Or watching the others eat it, at least. 

He ordered waffles one morning, pancakes the next. On the third he simply ordered fruit and a coffee. 

Jack had always loved breakfast foods. It was a good thing breakfast cereals weren’t on the menu here, or he might not be able to look at it. 

He filled his days with wandering. He visited a museum, trying not to hear Sam’s voice in his head rattling off obscure historical facts that he’d learned through his many hours of enthusiastic research. Trying not to remember watching history documentaries with him on Netflix. 

He saw an outdoor supply shop, and inexplicably thought of Dean. Perhaps it was the unbidden memory of being dragged into one such shop, late at night, while Sam and Jack finished with cleanup for a hunt. Dean’s spontaneity was a thing to behold sometimes. 

Everything reminded him of Jack. From the obvious, like children with their families on the sidewalk, to the seemingly random, like a song on the radio he’d never heard. It was as if Jack’s ghost was around every corner. Just waiting to pull at his heart, ripping at the broken pieces that were left. 

\--------

On the fourth day having breakfast in the restaurant, empty as was typical of the early morning, the waitress cleared her throat, shifting nervously as she brought him his food. 

Her name, according to the tag on her uniform, was Alina. She was young, slightly older than Jack looked. Around Claire’s age. Her eyes reminded him of Kelly. 

Cas looked up at her, wondering if he’d done something wrong, missed a social cue. Because apparently his friends thought everything that went wrong was always his fault. 

_Well, Dean did. Sam… who knows._

“I’m sorry, have I done something wrong?” he asked, trying to look as pleasant, as human, as possible. 

“Of course not,” she said, all in a rush. Sam would do that sometimes. Jack picked up the habit from him. “I just- I don’t mean to pry, at all, but I volunteer in a mental health awareness group, and I just wanted to make sure that you were okay?” 

It was a question. Castiel felt surprise, of all things. He hadn’t been sincerely asked if he was alright in quite a long time. Perhaps it was Sam… oh. No. It was Jack, he thought, after he’d used his powers to break Castiel free of the gorgon’s venom. 

“I… no,” he said, feeling strange. Emotional honesty was often hard to come by among Winchesters. Emotional awareness in general was hard to come by among angels. It was all still so foreign, and yet so natural. He’d always known how to feel, even if he hadn’t been allowed to for most of his existence. 

Alina nodded, expression sympathetic. “If you’d like to talk, my shift is over in a few minutes. I don’t have class for another two hours, so I can stick around.”

Castiel considered it. This was a simple kindness, from a young human woman to what she thought was a troubled human man. Maybe he was. Not quite, but more human than angel these days. 

He couldn’t really call himself ‘father’ anymore. Though that title had fit more comfortably than any he’d held in the past, perhaps even more so than ‘friend’. 

“I think I’d like that.” He hardly recognized the voice that spoke. It was too quiet, and quite weak. A far cry from the garrison captain that had flown proudly into Hell just a short decade ago. 

She smiled, a uptick of the lips that was gentle and kind. It made him think of Mary Winchester, of all people.

“I’ll be back in five minutes. Enjoy your food.” 

The five minutes passed quickly, though it was enough time for Castiel to begin to second guess. Alina sat down across from him, her hair down and name tag and apron removed. 

“I don’t want to trouble you,” Castiel started, feeling guilty all of a sudden. What had he done to deserve this kind of simple sacrifice?

“Kindness is never trouble,” she said. “Besides, I’ve been in dark places myself. It’s why I started volunteering with this organization in the first place. I don’t want anyone else to go to where I was.” Her hand drifted to her opposite wrist, absently, and Castiel thought he understood. 

He’d been there too. 

“Thank you,” he whispered. 

She nodded. “Of course.”

“I- I confess I don’t know where to start.”

Alina nodded. “That’s okay. Try your name? I’m Alina.”

“I’m… Clarence.” 

“Nice to meet you, Clarence. What do you do for a living?” 

“I’m… I’m an FBI agent. I’m, uh, taking some time off after I... “ he swallowed, trying to find the words. Trying to figure out how he could possibly say this. “After I lost my son.” 

“I’m sorry.” Alina settled a hand on one of his, where his hands were clasped until his knuckles were white. 

Castiel nodded. “Thank you. I also- my colleagues and I had a- disagreement. And a- a confrontation with management, you could say. It’s all just such a mess.”

“It’s okay. I know it doesn’t feel like it now, but if you think it would help to talk about them, I’ll listen.”

“What would you like to know?”

“Whatever you’re comfortable telling me.” 

“His name was Jack,” he said. “My- my son. He was… he was the best thing to ever happen to me. When he was born, his mother died, and I was… indisposed. My friends, they took him in. By the time I got back, I’d already missed so much. But holding him for the first time, it was like I’d found a piece of myself I hadn’t realized was missing to begin with. I never expected fatherhood. And I certainly didn’t know I could love someone so completely.”

It was true- he loved Sam and Dean, more than he knew how to express properly, but with Jack it was different. The force of his love for Jack was terrifying and powerful, and it scared him just as much as it soothed. It beat as steady as ocean tides, but it could hurt like a thousand knives. As it did right now. 

He missed him. So _much_.

He also hadn’t expected to confide to this extent in a woman he’d just met, but Alina simply nodded at him to keep going. 

“There was an accident. Jack, he- he hurt my friends, and then he tried in every way he knew to atone for it, but they hurt him back. I thought they’d have the strength to forgive him, to see that he was still good, still _him_ but apparently I was wrong.”

Betrayal was a bitter, rancid thing. Terrifyingly, it wasn’t a total surprise from Dean. But Sam… he’d been so close to Jack. Cas thought for sure Sam would have never allowed it. Sam had visibly been in pain when Chuck murdered Jack in front of them, and Castiel had seen him run far away from Belphegor at the earliest opportunity. 

It didn’t change it, couldn’t make up for what he’d done. And Castiel knew Sam regretted it. He did. He knew that someday Dean might get there too. But then Dean had proceeded to treat Castiel like he was a tool, the hammer he’d told Dean from the beginning he refused to be. And Sam didn’t stop it. 

“And then Jack- he- he died. And my friends blamed me for everything. One of them-” he couldn’t bring himself to say it. He held the Winchesters in very high regard. He didn’t like to speak ill of them. “It doesn’t matter,” he said instead. “The point is, they have each other. There was no reason for me to stay there any longer.”

That, he supposed, was the problem. Sam and Dean would inevitably choose each other, to the detriment of the people in their wake. It was admirable in a twisted way, and he’d always known on some level that loving them came with risks. 

He simply hadn’t expected it to hurt this much. He hadn’t expected himself to run. 

“This’ll be hard to hear,” Alina said. “But I think you did the right thing. Sometimes even the best friendships turn toxic at some point, and getting out, prioritizing yourself, is the best thing you can do. It doesn’t make you selfish. It makes you human.” 

Castiel exhaled, a weight being lifted from his shoulders. Perhaps he’d needed to hear that. 

“I don’t think I can ever stop caring about them,” he admitted. “Despite everything. Even when I can barely stand to think of them- they’re still my family.”

“That’s okay. One day, when you’re ready to try, maybe you could build that friendship up again. Forgive, but don’t forget. That’s been my life motto, and in my experience, it works.”

Castiel nodded. “Thank you.”

Alina smiled at him again, and Castiel found some strength to smile back. 

“I’ve, uh, got a list of books on grief somewhere on my phone, if you’d like them? Maybe that could help you find some footing.”

“I think I’d like that.”

He gave her his phone number, pulling it from his pocket as he did so. He went to open it up in order to view the message, and stopped short at the notifications on his screen. Sam had texted him. 

**Hey Cas, checking in.**   
**Didn’t realize you were taking off.**

They were from an hour ago. Another buzzed in as Cas watched. 

**Service sucks in the Bunker, want to make sure you’re getting these?**

That was interesting, considering service did not “suck” in the Bunker. He didn’t quite understand what Sam was implying. He did note that the second message indicated Dean hadn’t told Sam about what he’d said. 

Castiel really wasn’t surprised. When were Winchesters ever honest?

“Clarence?” Alina prompted. Apparently his face displayed his emotions. 

“I- one of my friends is contacting me. I don’t-”

“You don’t have to respond yet if you don’t want to. Give yourself time.” 

Castiel regarded the phone in his hands. Sam sounded worried, but Castiel really didn’t want to talk with Sam right now. He couldn’t rid himself of the image of Sam’s guilty face when Castiel arrived in the Bunker to find his son, _their_ son, locked in a living death. 

He cleared the messages, and then his breath caught. He’d forgotten. 

In his time in Goodland, he’d barely used his phone. Hadn’t needed to. He kept it charged out of habit, but he hadn’t once looked at it. 

On his lock screen was a picture of Jack. Sam had told him once that humans did that- put pictures of their loved ones as screen savers. Sam had a picture of himself with Dean on his home screen, hidden behind the array of apps there. Castiel had liked the idea, and so Sam had texted him a picture of Castiel and Jack, taken candidly when the four of them had been out to eat together. Castiel proudly set it on the phone. It was odd, since it was just for him, but he’d liked seeing it. Now he could barely stomach the sight, thinking instead of burning flesh under his hand. 

“Is that Jack?” Alina asked quietly. 

Castiel nodded, helplessly. He was grateful when the screen went black, taking with it Jack’s face. It was all too much. The memory of Jack, happy and alive and smiling like the sun, when Castiel was drowning in the wake of his failure to protect him. Not only breaking his promise to Kelly, but failing the child he loved as his own. 

He talked with Alina a while more, and when she had to leave for class, he thanked her profusely, shaking her hand. She just smiled, saying she was glad to be there to help, however she could. 

Castiel presented her manager with all the cash he had, asking him to add it to her tips. 

And then he drove. 

He wasn’t running, not anymore. He was going. Going someplace to find himself, find a semblance of peace in the whirlwind that was his life. He couldn’t stop the shaking anger inside him when he thought about Sam and Dean, nor the raw nature of the wound that was broken trust and hurt. Nor could he stop the gaping absence in his passenger seat and in his heart. 

He landed in Wyoming. He found a picturesque little town- not nearly as picturesque as Dodge City with its cowboys or Charming Acres with its milkshakes, or perhaps it was simply more lonely- and settled in. He spun a story similar to what he’d told Alina, but with less detail. He found a fishing shop, and thought of Dean, who consistently praised the activity. 

Cas thought he’d give it a try. 

He spent a few days fishing, thinking of how much Jack had enjoyed it when Dean had taken him. Castiel thought he understood why- he liked the peace, though he didn’t seem to be any good at it. 

Fishing, like most things, was probably better with family. 

A few days later he met a woman named Melly Krakowski. A woman whose son had gone missing. 

And he knew what he had to do.

**Notes for the Chapter:**

> Can y'all tell I'm a Cas girl yet? 
> 
> Anyway, I recently read a fic similar to this and it was really forking good, so like... if you liked this, give it a go? It's called "On the Road to Rishikesh" by AndThatWasEnough, and it's in my bookmarks. I loved it, and I feel like I need to mention it here because I'm pretty sure it half-inspired this chapter? If you do check it out, bring tissues with you. 
> 
> Thanks for reading! I'd love to know what you thought!


	6. Please...

**Summary for the Chapter:**

> Day 6: No More  
> Whumpee: Bobby   
> Set during Bobby's time in Hell, between when they burned his flask and when Sam went to get him in 8x19. Some references to both those things.   
> Also, warning for mild body horror.

Bobby Singer was no stranger to pain. His childhood had been so far from a walk in the park it may as well have been a drag up a gravel drive. Being a hunter came with gunshot wounds you poured whiskey over and stitched up yourself in a dirty bathroom. Physical pain he could handle. It was the rest that he had to bury. 

Karen. He still couldn’t think about her, especially after the second time. 

Rufus. They’d been through a lot, and Rufus hadn’t deserved to go out the way he had. 

And his boys. He shouldn’t have even had kids, but somehow he got stuck with two idjits. And he’d had to watch them both die. 

One minute he’d been watching his boys’ faces for the last time as he felt flames lick at his essence, eating him up and banishing him from earth, and the next he was chained to a wall and staring into Crowley’s face. 

“The _hell_?” Bobby spat. He was supposed to have some goddamn peace if he wasn’t able to help, and Crowley was about as far from peace as a person could get. 

“That is correct. Good to know you’ve still got a brain left after all that whiskey. I don’t have much time right now- you know, Leviathan Apocalypse impending and all- but I did want to be here to personally welcome you. Hell’s a lovely place, if you give it a chance.”

“Somehow that don’t sound right, but I’d love to take your word for it.”

Crowley smirked. “Oh, don’t worry- you won’t have to. You’ll have plenty of time to form your own opinion.” 

Crowley blinked out, leaving Bobby chained helplessly to the wall. 

While this wasn’t a picnic, it definitely wasn’t what he thought Hell would be like. Not given Sam’s hallucinations and Dean’s nightmares and drinking after they’d been down here.

The silence stretched on, long and empty. Occasionally it was punctuated with violent, agonized screams or demonic laughter. Eventually Bobby’s limbs numbed. He was left a floating knot of regret and bad memories, a few good ones here and there.

Maybe that was his torture. 

An indefinite stretch of time later, and something actually happened. 

The sounds of a scuffle came from outside his cell, and then the last person he’d expected to see stood in his doorway, a bloody angel blade dangling loosely from one hand. 

“Dean?” 

Dean grinned up at him through a bleeding cut on a split lip. “Hey, Bobby. Sorry we’re late.”

Dean came up to him, that wild grin still on his face, and he started working on the chains. 

“Man, is it good to see you, Bobby. When we heard from Crowley that you were down here…” Dean snapped one of the chains out of the wall, with much more force than necessary. “Well. You get the picture.”

“The hell are you doin’ here, boy?” 

“What do you think?” The last chain snapped, and Dean steadied Bobby with a hand on his shoulder, squeezing. “We’re bustin’ you out, Bobby.” 

In a blink, a knife impaled itself in Dean’s back, sending him, eyes wide, reeling to the floor. Bobby looked up, jaw dropping when he saw Sam standing there, grinning, arm outstretched where he’d thrown the knife. Then Sam's eyes flashed black, and he was walking towards Bobby, pulling out another blade.

That’s when the physical torture started. 

\--------

Bobby knew what was happening. Knew the real Sam and Dean were still topside, hopefully back to plain-jane hunts after dealing with the Leviathans. Down here, demons in Winchester look-a-like meatsuits taunted him all day long. 

Half the time it wasn’t even him they were hurting, but watching Dean gouge out Sam’s eyes with a grin on his face or Sam pull out Dean’s intestines while laughing like the Devil was still in him was actually worse. 

Not worse than his idjit kids actually _looking_ like kids. The snot-nosed little buggers they’d been when he met them would get ripped apart in front of his eyes, or sit on his shoulders and bite off his ears. 

He had to hand it to Crowley- this wasn’t what he’d expected, but it was damn effective. 

Bobby was nothing if not determined, though, and he wasn’t gonna give in to that smarmy bastard if it could be helped. Which it could. 

He sat and took it. Watched his boys break apart, rip each other to pieces, grit his teeth through their blades and bullets and fingernails and barbed words and just took it. 

Wasn’t a thing to do about it.

Eventually, he started fighting back. Punching, kicking, the works. Most of the time the demons would break character, which made Hell a hell of a lot more bearable. 

One day, maybe centuries later, he punched the Sam skinsuit that entered his cell. And it turned out to be the real Sam, actually come to get him. Obviously Bobby’d wanted the torture to end, but he thought that would be when he eventually got recycled into the universe, all new age-y garbage style, or when Crowley got tired of wasting demon power on him and fed his soul to some Hell creature. 

Funny enough, a Trial-of-God taxi to Heaven hadn’t really crossed his mind. 

At least he’d finally get some peace and quiet, though it wasn’t what he really wanted. 

No more of this afterlife crap. What Bobby really wanted was to be back, fighting the good fight with his boys. 

Apparently, the universe had other plans.

**Notes for the Chapter:**

> So, I'm not really happy with how this turned out. I don't really know why but it didn't match up with whatever I thought it was going to end up being. Oh, well. 
> 
> SIDE NOTE, I'm SUPER excited for tomorrow's prompt. Stay tuned! ;)


	7. I've Got You

**Summary for the Chapter:**

> Day 7: Support  
> Whumpee(s): Sam, Jack  
> Set early season 13, before Cas comes back in 13x06.  
> And I'm gonna be honest- this isn't whump. It's pure fluff with a pinch of angst. Enjoy :)

Sam walked down the Bunker hallway, planning on stumbling into his room and attempting to sleep for a while. He’d been in the library, trying to battle his insomnia by reading until his eyes were too tired to stay open, but it hadn’t really worked. And though his body was tired, he knew if he shut his eyes he’d just see mom going through the portal, and the blade coming through Castiel, his body dropping and Lucifer standing there grinning. 

Sam shuddered, leaning on the wall. No time to think about that, not when he could always find work to do. 

In the silence, Sam heard the short, heavy breaths indicative of sobs. They were coming from Jack’s room. 

Rapping his knuckles on the door, Sam called out softly. 

“Jack?”

The sobs stopped, much too quickly. “Come in.”

“Hey, buddy,” Sam said. “I just thought I’d check on you. Are you uh- you doing okay?” 

He’d just have to hope Jack didn’t call him out on his reasons for the check in. 

“I’m fine,” Jack said in a small voice. A Winchester already. Great. 

Sam moved to sit on the edge of the bed. 

“Can’t sleep?”

Jack nodded, pulling his knees up to his chest and hugging them. 

An idea hit. He’d just have to hope that Dean was drowning himself in whiskey in the privacy of his room tonight. 

“Hey, come with me. I’ve got an idea that might help you sleep.” 

Jack looks up at him with those wide blue eyes, blue like Castiel’s. Well, not Castiel’s, but it’d been him behind them for years. Jack looked like Cas, which really didn’t make sense. Jimmy Novak’s DNA wasn’t anywhere in the kid’s code, couldn’t be. It was just one hell of a coincidence. 

Jack slid off the bed, an arm wrapped around himself, and he followed Sam to the kitchen, his feet scuffing as he went. Sam walked to one of the upper cabinets, where he kept his boxes of tea. He pulled out chamomile and a bottle of honey, and then started filling the kettle. 

“You haven’t had tea yet, have you?” 

Jack shook his head, watching in fascination as Sam put the kettle on to boil and then selected two mugs. 

“What is it?” Jack asked. 

Sam paused. How was he supposed to explain tea?

“It’s- well, it’s hot water with herbs in it. Like an infusion. Some kinds are really calming, and they can help you relax and go to sleep.” 

Jack nodded, but he still looked confused. 

Sam tried to smile. “Just try it, Jack. I think you’ll like it.” 

The kettle was done, so Sam filled the two mugs. He spooned some honey into each, stirring till it dissolved. Jack came and watched from behind him. 

“What does honey taste like?” 

Sam opened the box of chamomile, selecting a tea bag for each mug. 

“It’s sweet. Cas- Cas liked it a lot.” 

“Do you like it?” 

Sam paused, surprised Jack wanted his opinion. He'd thought name-dropping Cas would be enough of an assurance. 

“Yeah. Yeah I do.” 

Sam put the box away and grabbed the mugs, walking over to the table. Jack followed, sitting opposite him. 

Sam slid a mug across the table to Jack. 

“It’s hot, so you’re going to have to let it cool before you can drink it, okay?”

Jack nodded and tentatively wrapped his hands around the mug. 

“Why are you doing this?” Jack asked, his voice soft. 

_Because I’m scared of you. Because I think your powers can get my mom back. Because you remind me of my dead best friend. Because no one was there for me when I was scared I was evil._

“Because I’ve got you, Jack. Okay? Whatever you need, I’m there.” 

Jack’s lips quirked up, and he took a sip of his tea. He squinted his eyes like Cas with PB&J. 

_Don’t think about that._

“I- I like it!”

Sam smiled. “That’s good, Jack. I’m glad.” 

So they sat, sipping their tea. Eventually, Jack spoke. 

“Sam? Do you ever- feel like your mind is just too loud? And you can’t go to sleep?” 

“All the time.” 

Jack looked surprised. “Really?” 

Sam nodded. “Yeah, Jack. At night, when it’s quiet, the things you want to forget come back. It’s okay if it’s hard to rest sometimes.” 

“How do I make it go away?” 

God, there were tears in his eyes. They went straight to Sam’s heart. 

“Little things. Strategies, they help. Like tea, or meditation, reading- we can work on those. But sometimes, the best thing you can do is just talk about it.”

“Do you ever talk about it?”

Sam’s mouth went dry. “S-Sometimes.”

Jack leaned over the table and patted Sam’s arm, a gesture likely learned from his Dean mimicry. 

“I’ve got you, Sam,” he said sagely. 

Sam didn’t doubt it. Here, sipping tea with this kid, Lucifer’s kid, Cas’s kid, who was slowly becoming Sam’s kid- he could be sure of one thing. 

He and Jack would have each other.

**Notes for the Chapter:**

> Sam and Jack are just so good. Ahhh. Cas'n'Jack has my whole entire heart, but Sam'n'Jack is like... VERY close behind. (and tbh the beauty of it is that they both coexist at the same time, because Jack absolutely has room for all the parental figures who are just gonna love him and support him like he deserves. And BOTH father son duos are fantastic. No question).  
> Anyway, I hope y'all enjoyed! Reviews are always welcome, and very much appreciated :)


	8. Where Did Everybody Go?

**Summary for the Chapter:**

> Day 8: "Don't Say Goodbye"  
> Whumpee(s): Sam'n'Dean  
> Set across various episodes

When the doctors told Sam “heart failure,” he simply couldn’t believe it. It didn’t fit. Those words didn’t belong in the same paragraph- hell, on the same page- as Dean’s name. 

But seeing Dean in that hospital bed, pale and shaky, like breathing was an effort, made it all real. 

Sam wasn’t about to let Dean die. Not in a million years, if he had a thing to do about it. 

Heart failure wouldn’t take Dean. 

——-

A car crash wasn’t gonna get Dean. Sam knew that- there was no way Dean would _let_ it be a car crash- not cool enough. Didn’t fit his macho image. 

When Dean nearly left Sam, the doctors crowding around and shocking him, Sam standing helplessly in the doorway, his heart was in his throat. Because what if Dean did go out like this, when they were just starting to be brothers again? 

No. He wouldn’t. Sam could feel him here, and Dean was too stubborn to die this way. It’d be okay. 

Sam wouldn’t have to say goodbye. 

——

Sam going cold in Dean’s arms was easily the worst feeling he’d ever experienced. He felt- he didn’t even know how to describe what he felt. Hollow, empty- but somehow in agonizing pain. He held onto Sam’s body for dear life, screamed into the night- and of course it didn’t do any good. 

When it counted, Dean hadn’t been there to keep him safe. 

Gone. Sam was gone. And it was all his fault. 

——

Sam didn’t know what day it was anymore. Maybe Tuesday 46? Yeah. 46. 

God. 

Sam didn’t have the energy to move. So he just laid there. Dean was in a frenzy beside him, but Sam couldn’t move. Didn’t want to. 

If he didn’t move, maybe he wouldn’t have to see it, hear it, feel it, or even smell it when Dean died this time. 

He couldn’t do this anymore. 

——

The mystery spot couldn’t possibly have prepared him for this. Sam cried over Dean’s body, blood from the hellhound claws dried on Sam’s hands and the floor of the house. The body Ruby was using lay prone on the floor a few feet away. 

Eventually Bobby came by, trying to pull Sam away. He just held tight to Dean’s body, his heart shattering into pieces. 

He couldn’t say goodbye. 

——

Everything reminded him of Sam these days. Lisa played a song he’d heard Sam listening to. Ben ate a peanut butter and banana sandwich for lunch one day. Joggers on the sidewalk, produce aisles in the supermarket…

The impala. 

So he covered her with a tarp, let Lisa do the veggie shopping, and made Ben plain PB&J sandwiches. 

Dean would be fine. 

He just had to figure out how to say goodbye.

——

Exploded. Dean and Cas had just exploded. Dick Roman was dead, but so were they. No. No.

_No._

Sam got in the Impala and started driving. Aimlessly. He drifted into the other lanes, got honked at countless times, and nearly flipped the car. At one point he had to pull over and squeeze the scar on his palm, taking heaving breaths through his tears. 

He hadn’t gotten to say goodbye. He hadn’t even been there, and they were gone. After regaining a fragile semblance of composure, Sam kept driving. And he hit a dog. 

It snapped him out of whatever mental fog he’d been stuck in. No one else would get hurt because of him right now. Not even a dog. 

He couldn’t fail anyone else. Not again. 

——

It was strangely beautiful, but so wrong. The angels were falling. Dean spared a thought for Cas, but Sam was more important. As Sam cried out in pain, Dean trying to get him into the car, panic struck. 

He couldn’t lose Sam, not again. Not ever again.

He’d do whatever it took to keep from saying goodbye.

\------ 

“I’m proud of us,” he’d said. Proud of what?

Sam had to pull the car over on the way back to the bunker. He rested his forehead on the steering wheel, white-knuckling the sides of it. He couldn’t do this. Not again. 

If Dean was really dead, Sam had wasted their last year being mad at him. But he was never _not_ going to be mad at Dean for what he did, for what he _allowed_ to happen to Sam. 

That didn’t mean Sam stopped loving his brother. Broken trust didn’t mean thirty years of love went up in smoke. 

No. Sam wasn’t going to give up now. He was gonna summon Crowley’s ass and make him fix this. 

Sam pushed the pedal to the floor on the way back to Lebanon.

\------

It wasn’t fair. This was just- absolutely ridiculous. 

Cas was trying, and Sam appreciated it much more than he was showing. He felt kind of bad about it, but he was stuck in his own mind. 

Then some blond woman banished Cas, and Sam was jolted out of his funk. Cas was quite literally all Sam had left, and he wasn’t gonna stand for his friend getting hurt. 

And then all Sam knew was pain. 

At least he had something else to worry about besides grief. He didn’t think he could manage it otherwise. 

\------

It was so bloody. And it was imprinted on Dean’s eyes, forever. The image of his little brother getting his throat ripped out- 

_Stop._

He shut himself down. It was better than trying to interact with anyone, because if he did he’d snap. 

He’d yell at Cas, who probably didn’t deserve it. Dean knew, somewhere inside, that Cas was probably devastated too. He’d been the one to run after Sam down that tunnel, after all. But he still pushed him away from Sam’s body. 

That girl came up to him, said, “I’m sorry about your friend.” 

Dean glared at her until Cas pulled her back. 

_I’m sorry about your friend._ Ha. 

Sam was his friend. Sam was his brother. Sam was his family. 

Dean didn’t have a fucking clue what to do now. 

\------

When Jack healed Sam, Dean walked away. He couldn’t do this. God- he’d almost- 

_You always put me first…_

He took a deep breath, because he had to. He had to keep going, had to be okay. Sam was fine. He didn’t have to say goodbye. 

_I don’t know how to say goodbye._

**Notes for the Chapter:**

> Hope you enjoyed!   
> Also, season 15B starts today and I for one am very excited. Even though I can't actually watch the eps until Fridays. If you're watching live too, best of luck. I know my stress levels are THROUGH THE ROOF.


	9. For the Greater Good

**Summary for the Chapter:**

> Day 9: "Take me instead"  
> Whumpee(s): Castiel, Kelly Kline  
> Missing scene from 14x08, after Cas makes his deal with the Empty.

Kelly watched as Castiel lowered his hands from where they’d been cupping Jack’s face just moments before. Her son was safe now, resurrected and in a repaired body. She had to believe that. Castiel seemed to. 

She watched as his face fell into something unreadable, something ancient and sad and yet somehow resolute. 

“Castiel?” she asked, moving towards him to settle a hand on his arm. 

He snapped out of it, sparing a ghost of a smile for her. “I- uh. I should be going back. It’s a fairly long drive, and I-”

“It’s okay,” Kelly said, smiling gently at him. 

“I- I don’t regret what I did. I could never- Jack is-”

“I know.” 

And she did. She’d only just met him, but she knew that Jack was amazing. So sweet and kind and earnest, just like she’d imagined he’d be from what she could feel while she’d been pregnant. And she certainly understood being willing to die for him, since she’d done so just to bring him into the world. And if Castiel was willing to do the same to keep him there- well. She was beginning to suspect that ease of sacrifice was just something that came with being a parent. 

“Are you alright?” she asked, looking at him. _Really_ looking. 

“I’m sure I will be,” he replied, voice tired and drawn, eyes sad but laced with love. “I think I just need some time to- adjust. To living with this looming over my head.” 

“Believe me, I understand. But, somehow- it isn’t all bad. Just cherish the time that you have with him. In a way, it makes it sweeter. And you never know- it might not be the end.”

The corner of Castiel’s lips quirked up, sardonically. “Well, for me it will be. That’s what- that’s what makes this so hard.”

Kelly didn’t know what to say, so she just pulled him in for another hug. She’d be alone for a while now, after all. 

“I’d do it again. In a _heartbeat_.” 

Kelly squeezed tighter. “And that’s why you’re amazing too, Castiel.”

He pulled back, Kelly raising on tiptoes to kiss his cheek. 

Castiel took a hesitant step towards the door, turning back once his hand was on the knob. 

“I’ll look after him.” His voice was full of that resolve, that righteous protectiveness and paternal love it made her endlessly happy to see. Fatherhood was good for him. Even if it killed him. 

“I know. But look after yourself too.”

Sad, old blue eyes smiling at her. “I- I will try.”

Castiel opened the door, stepping outside. She couldn’t stop herself. 

“Castiel!” 

He looked back at her. 

“Maybe… you could come and visit me sometime?”

Another smile, a gentle one. And yet the saddest of them all. “Oh, Kelly,” he said. “Nothing would make me happier.”

She supposed she should be honored. That she and Jack could somehow be capable of making a timeless being happy. All she felt was sadness. That she couldn’t do more for her friend. The guardian of her child. 

“Goodbye, Castiel.”

“Goodbye, Kelly.”

And then he was gone, disappeared into the long white hallway, off to go home to her son. Their son. And she’d likely never see either of them again. 

If you’d told Kelly Kline when she was a little girl, one with dreams of working in the White House and being a mom, that she would not only accomplish both of those things but also befriend Heaven’s best angel, she never would have believed you. 

Of course, she never would have believed you if you’d said she’d be crying in Heaven, either. 

Yet that was exactly what she did.

**Notes for the Chapter:**

> I just really love Kelly Kline, guys. And this got real sad real fast. I guess that's the goal, but writing this one really took a lot out of me emotionally. 
> 
> Thanks for reading!


	10. They Look so Pretty When They Bleed

**Summary for the Chapter:**

> Day 10: Internal Bleeding  
> Whumpee: Sam  
> I honestly have no clue when this is set. Let's say it's an ambiguous place where Jack for whatever reason can't use his healing powers, and TFW just chills in the Bunker being domestic for extended periods of time.   
> Also, medical inaccuracies abound! Because I have absolutely no idea what I'm doing. Googling symptoms can only get somebody so far.

Sam got thrown around on the daily. Unfortunately. Usually, he didn’t think anything of it. A few bruises and scrapes here and there, not usually a big deal. He’d taken to regularly checking his pupils to make sure he didn’t have a concussion. He tried to eat well, stretched, exercised. Did his best with what he was given. 

They’d had some down time in the Bunker for a few days, and Sam was feeling off. He figured he was probably just overtired, and so he tried to take it easy. Eventually he had to stand up and get something to eat, though. But when he pushed off his bed, he was met with a rush of dizziness and nausea. Taking a shaky breath, he kept walking. Maybe no food, just water. He didn’t get sick. He really hoped he wasn’t sick.

Jack was sitting at the kitchen table with a book and a mug of tea. Sam smiled. Jack had found him drinking tea once and been so eager to try it, and then Cas had expanded on his obsession by showing Jack that he could put honey in it. Now both resident cosmic beings used way too much. Sam wasn’t worried for Cas, since he didn’t need food anyway, but it couldn’t be healthy for Jack to be having that much. 

Jack looked up and smiled. “Hi, Sam!”

Sam leaned a little bit on the counter, his head spinning. “Hey, Jack,” he managed. 

“Are you okay?” Jack was frowning now, brow furrowed and book forgotten. 

“Yeah, I- I’m fine, Jack, don’t worry.” A fresh wave of dizziness. 

Jack was a lot closer now, but he was still blurred. “You’re bleeding,” Jack said, eyes wide. 

Sam groped a hand up to under his nose, where a stream of blood was trickling down. 

_Huh._

Sam’s legs gave out in a spasm, sending him crashing to the floor, half-propped up against the cabinets. Jack yelped, coming down with him. “Sam!”

Jack’s hands hovered by Sam’s arms, unsure of what to do. Sam threw himself to the side when the nausea struck, knowing what was coming and trying to avoid getting any vomit on Jack. His ears rang, and he was dimly aware of Jack yelling for Cas and Dean. 

Footsteps sounded from the hall, and Dean’s boots came swinging into view where Sam lay panting on the floor. Dean tried to haul Sam up with an arm around his torso, but when it came into contact Sam grunted in pain, trying to shake his brother off. 

“Jack, go, get Cas. Now!”

Sam’s head was spinning so fast he could barely see. He wondered how he’d understood Dean’s words at all.

\-------

Castiel sometimes came outside to think. He enjoyed being surrounded by nature, liked the beauty and serenity of it. So when the Bunker door came flying open, Jack running outside, panic on his face, Castiel was instantly alert. The peace was broken. 

“Jack, what’s wrong? Are you alright?” 

“Something’s wrong with Sam,” Jack said, breathless, and the two of them sped back into the Bunker, Cas following Jack’s lead to the kitchen. The scene that greeted them was dismal- Dean hovering over Sam’s prone body, blood dripping from Sam’s nose and mouth onto the floor, next to the pile of bloody vomit emitting a coppery stink. 

“Can you fix him?” Dean asked, face hard but eyes terrified. Jack stood to the side, wringing his hands. 

Castiel crouched beside his friend, hand hovering over Sam’s forehead. “I think so,” he said, in response to Dean’s question. “He’s bleeding internally.” Though he stated it as a simple fact, Cas was surprised. He didn’t think Sam had encountered any kind of blunt trauma today that could cause such a thing. 

As Dean set to sputtering in incredulity, Castiel got to healing. Sam shot up, eyes wide, wiping the blood from his face. 

“Cas? Dean? What- what happened?”

“You were bleeding internally,” Castiel supplied. Sam blinked at him. 

“I was what?”

“You were bleeding internally,” Cas repeated, while Dean scrubbed a hand down his face and Jack inched closer. 

“Oh. I guess it must have happened during the last hunt.”

“The last hunt?” Dean said. “The last hunt? You tryin’ to tell me you’ve been walking around with internal injuries for four days?”

Sam shrugged. “I guess so?” 

Dean turned away after a quick pat to Sam’s shoulder, which belied his actual relief and concern, walking out of the kitchen. As he went he tossed back, “Unbelievable. And you’re cleaning the goddamn floor!” 

Sam glanced at it, nose wrinkling in disgust. Castiel waved his hand and it disappeared. 

“You can do that?” Sam asked him, accepting Jack’s help to stand. 

“Do what?” Castiel asked, head tilted. 

Sam huffed a laugh. “Thanks by the way.” 

“Yeah, of course. Next time, don’t get hurt.”

“I’ll try.”

**Notes for the Chapter:**

> I'm not super happy with this one either. Apparently I really struggle with like... physical torture whump. Emotional and psychological I can do, but this is hard. I hope it was okay anyway.
> 
> Thanks for reading!


	11. Psych 101

**Summary for the Chapter:**

> Day 11: Defiance  
> Whumpee: Castiel  
> Set pre-series to season 4/5 ish. You know, Apocalypse days.

Naomi had a critical job in Heaven, and she was proud to complete it. She only wished she did not have to as often as was required. 

There were the usual problems, who required constant correction. Anna, Balthazar. Anna was too headstrong, too independent. She sought to do things her way. Naomi helped her remember that angels did not have individual ways of doing things. Balthazar rebelled because he enjoyed chaos and human indulgences. She suspected he found some kind of beauty in the chaos he caused, but he was still too much like Gabriel. Unlike with Gabriel, however, Naomi could fix Balthazar. And so she did. 

Her biggest problem, though, was Castiel. She was sure he’d been made broken, because he was always feeling _something._ When they were ordered to perform a mass smiting, or cause a plague, Castiel always complained, or vouched for the humans. Said that they had the potential to grow, to do better, to choose. 

He required _constant_ correction. 

The first time, Castiel and Balthazar had been brought before her, as fledglings who had tried to sneak down to earth. Apparently the first taste of God’s creation hadn’t been enough, and so they wanted more time. They didn’t realize that earth was to be observed, not touched. That lower life forms were for look, not play. 

It was both of their first corrections. Balthazar took it in stride, surprisingly, while Castiel fought all the way. 

\---------

The worst was when Castiel befriended a human, at about a million years old. He’d been assigned to take a vessel, and when a lowly, dirty human begged for help, Castiel fought against his own siblings. He’d been dragged back to Heaven quite literally, strapped down in Naomi’s chair. Zachariah and Raphael demanded the harshest of corrections, and Naomi was happy to oblige. This kind of behavior was unacceptable. 

“I don’t know what’s wrong with you, Castiel,” Naomi said, circling him. Castiel simply glared. “You must have been made incorrectly. Born broken. I can patch you up as best as I can, but this kind of defiance will help no one. It will certainly not help God’s plan be carried out.” 

“God asked us to love humans,” Castiel said, as if it were that simple. “And so I do. They are beautiful, and they are capable of so much kindness. So much more than us. If I am broken for believing in that, then I am proud to be so.”

The correction was harsh. Castiel’s screams were powerful enough to move mountains and destroy human villages. It had to be done- his memories of his human friend purged. 

Castiel did not rebel outright for many more years, and never in a way so direct. But Naomi could see the averted gaze, the whispers with Balthazar and a few others. Still, Castiel was a good soldier. If he needed to be steered to stay on course, so be it. He was strong and his faith was true. He just had too much sympathy, grieved a bit too much for fallen siblings. 

Nevertheless, he rose through the ranks. When the siege of Hell for the Righteous Man was organized, Castiel’s garrison was chosen. Naomi listened as Castiel shouted with pride that Dean Winchester was saved (too much pride, too much feeling) and tracked his progress in assisting his charges. 

They should have seen it coming. 

Despite all her painfully careful instruction, Castiel touched the abomination. Shook hands with the Boy with the Demon Blood. 

He was reprimanded for that. 

Castiel objected to using Dean Winchester’s torture skills on the demon Alastiar. He refused to use violence against Sam Winchester when he needed to be subdued. 

He was strongly reprimanded for that. 

Still, he continued. When it became clear he had established a friendship, yet again, with a human, they pulled him back. He stared Naomi in the eyes, defiance in every facet of his form. 

“Dean Winchester is my friend,” he said. “And Sam Winchester is an abomination, yes, but not by choice. Perhaps with some guidance-”

He did not finish his sentence. When he returned to earth to reclaim his vessel, he knew better than to play nice with Dean Winchester and his abomination of a brother. 

She’d thought they had Castiel secured, loyalty tightly bound where it should be. 

She was wrong. Castiel rebelled, again, fully, much more fully than before. He was lost, his unseemly predisposition to feeling and humanity tearing him away. 

Naomi had always known Castiel was different. She’d thought she could fix him, but she was so very, very wrong. 

Because what was built wrong could never be fixed. The broken mess of an angel that Castiel was had fallen so far that he was what he would once have called an abomination. 

And Naomi knew that he likely didn’t regret it, still didn’t see that his true family only wanted him back where it was safe, and they could do their jobs together. 

Too much heart. Too much feeling. 

Castiel’s problem became his downfall.

**Notes for the Chapter:**

> Pre-series Cas is just so interesting! How many times did he have to be reprogrammed? Did he have any other human friends? How many years is he missing because they were taken away? I have so many questions. And I just really love Castiel. 
> 
> Anyway, I hope y'all enjoyed!


	12. I Think I've Broken Something

**Summary for the Chapter:**

> Day 12: Broken Bones  
> Whumpee: Jack  
> Early season 14, Jack has a soul but no powers. Let's say it's an AU where, after 14x06, Jack lasted a little longer before. You know. Dying.

The thing about having no powers was that he thought about it. Constantly. Every moment Jack could feel the absence in him where his grace used to be, always hollow, sometimes aching. Food tasted different, he got tired easily, and everything _hurt_. He didn’t understand how Sam and Dean could do what they did without grace. Or any hunters. It must hurt so much.

Not that he’d ever tell that to Sam or Dean or Cas, because then they’d never let him leave the Bunker again. 

Jack was happily out with Dean on a hunt right now. He was finally starting to feel like Dean didn’t hate him, which was good. Jack didn’t want to be a dividing force in his family any longer. He didn’t like hurting people, and he liked hurting his family even less. He hated it.

They were hunting a demon in Topeka, Kansas. It was only a few hours’ drive from home, so Dean had let him come along. Sam was helping Maggie wrap up one of her hunts in northern Oklahoma, and Cas was staying in the Bunker to “hold down the fort.” 

Jack didn’t quite know what that meant, but he was glad he could do this alone with Dean, maybe impress him. He _really_ wanted Dean to like him, and think he was just a capable a hunter as anyone else. 

Jack wiped sweat from his palm and tightened his grip around his angel blade. Dean looked back at him and nodded, once, before pushing open the door to the old cabin on the outskirts of town the demon had apparently “set up shop” in. Renegade crossroads demons were one of the things Dean called a “milk run,” so Jack was hoping he could really do well on this hunt. 

He should have just stayed home. 

The demon had been expecting them, and threw Dean and Jack to opposite walls as soon as they walked in. Jack’s blade was thrown far from his reach.

The demon held Dean against the wall with its telekinesis, and advanced on Jack. He tried to scramble to his feet, but his head was pounding. The demon laughed. 

“Well, well,” she said, looking down at Jack through her stolen body’s long hair. “Look at you. The little nephilim baby, reduced to nothing. And what a weak little nothing you are.”

She waved a hand, and Jack felt himself get held in place by invisible power, arms splayed out to his sides against the cabin wall. The demon flicked a knife out of her sleeve, trailing it over Jack’s cheek, enough for the cold metal to sting but not draw blood.

“Hey, hey! Get away from him, bitch!” 

She snapped her head back towards Dean, a malicious grin spreading across her face. 

“Okay,” she said, too cheerful. Jack didn’t like it. “I will.”

She did step back, and then, out of nowhere, brought her foot down on Jack’s thigh. Hard, with the force of all her demonic strength behind it. Jack screamed. 

It was unlike anything he’d ever felt before. The crack of his bone was loud, and made much worse by the knowledge that it was his leg breaking. Beyond that, he could feel it shifting around inside when she lifted her foot, and then the pain didn’t subside. It got worse, as Jack was trying to instinctively pull away. 

When he finally opened his eyes again, all he saw was Dean plunging his blade into the demon’s stomach. In the haze of pain, Jack hadn’t seen how Dean had managed to get away from the demon. 

Dean was sliding down beside him, looking at Jack’s leg like it was something gross. Jack followed his gaze, and immediately wished he hadn’t, because he could see a little piece of his bone sticking out. 

Nausea flared, and he squeezed his eyes shut again, biting his lip. 

“Hey, kid, don’t look at that. Look at me.” 

Jack did, fighting to keep his eyes dry and his breathing steady. Dean looked him in the eyes, steadfast and somehow calm. As if Jack wasn’t in the most excruciating pain of his life. 

“I don’t think we can move you right now, kid. Or call an ambulance, because that-“ he gestured to the dead body across the room. “-would be hell to explain. So what I’m gonna do is call Cas, get him to run his feathery ass over here. He’ll heal you right up. Okay?” 

Jack knew he was expected to respond, so he nodded, choking out an “okay,” of his own.

“You’re doin’ great, Jack. I’ll be right back.” 

And then Dean was gone, and somehow being alone like this was a thousand times worse. He was just so stupid to think he could do anything like this without powers. Because without them he really was just a dumb child. A dumb, breakable child. 

Dean came back in, pocketing his phone. 

“Cas is on the way. Pissed at me, probably. But he’ll be here soon.” He sighed, sliding down the wall to sit next to Jack.

“Why-“ Jack had to fight to keep his breathing steady, ignoring the tears that slipped out the corners of his eyes. “Why is Cas- mad at you?” 

Dean gave him a look Jack didn’t know how to interpret. “‘Cause you got hurt on my watch, kid. Doesn’t matter. It’s probably more worry than fear. And hey.” Dean reached into his jacket pocket, pulling out a flask. “Drink up.” 

Jack stared at it. “Why?” 

Dean grinned. “Old fashioned medicine. It’ll help stave off the pain for a while until Cas gets here. Just trust me.” 

Jack accepted the flask, warily. He took a gulping sip, expecting something that tasted like beer. He didn’t really like beer, but drinking it was something his family did together, so he learned to like it at least a little bit. This was different- it was like fire on the back of his throat. He coughed, and it jarred his leg, turning the cough into a yelp.

“Easy, easy.” Dean eased him back against the wall. “Yeah, that’s the strong stuff. Gotta be careful with that.” 

Jack took a few more tentative sips, feeling better once his limbs started to tingle with numbness. 

“Okay, that’s enough.” Dean yanked the flask away. “I give you any more of that and Cas’ll really kill me.” 

Jack frowned. “He wouldn’t kill you. He’d never hurt you, or Sam, or me. Because that’s not what family does.”

Dean snorted. “Figure of speech, Jack. Gotta learn those.”

“Oh. Sorry.” Now he felt like crying. He wasn’t normally this childish. What was wrong with him?

“Jack. I didn’t mean it like that, okay? You just have to work on it. We all have things we have to keep working on.” 

“Yeah?”

“Yeah.” 

They sat in a silence for a long while, Jack listening to the buzzing of his blood in his ears. Whatever was in Dean’s flask was working really well. 

“Hey, Dean?” That was weird. Jack’s voice sounded like it was underwater. 

“Yeah, kid?” Dean sounded like he was underwater too!

Jack laughed. “Have you ever broken a bone before?”

“Shit, you’re really smashed.” Smashed? Jack didn’t know that that meant. He laughed again, his head swimming. This wasn’t so bad. Oh, wait. Dean was talking.

“...but I have broken my leg before. Was laid up for weeks, couldn’t do a damn thing.”

Jack frowned. “Cas didn’t fix it?”

“Ah, well. Cas wasn’t around at the time.”

“That doesn’t make sense.” 

Dean laughed. It didn’t sound like he found it funny, though. It was a painful laugh. “Yeah, to you it wouldn’t.” 

“Do you hate me?”

Dean stiffened. He took in a deep breath, while Jack held his. 

“No. God, no, I don’t hate you, Jack. I just- you’re a good kid. I wasn’t. I was never a kid, period. So sometimes I need a little time to figure things out. But I’m gonna try my damndest to protect you, okay? Because you are family. And that’s what family does.”

Jack smiled and closed his eyes. He wanted to go to sleep. “I’m glad we’re family.”

He almost missed it when Dean said, “me too.”

Then the door slammed open, and in walked Castiel. He ran, actually. Jack smiled and waved at him. 

“Hi, Cas!” 

Cas stopped short, looking from Jack to Dean. “Did you get him _drunk_?”

Dean shrugged. “Field medicine.” 

Cas just glared at him. 

“Fine, fine. I’m sorry. But he isn’t in pain anymore, right, kid?”

“Right!”

Cas sighed, kneeling down next to Jack and pressing his fingers to his forehead. With the calming flow of grace came clarity, as he washed away the alcohol and fixed his leg simultaneously. 

“Are you alright?” Castiel’s eyes searched Jack’s face for any sign of distress.

“I’m fine.”

Dean and Cas helped Jack to his feet, where he didn’t so much as wobble. Jack looked at Dean and smiled, pleased when he got a small smile in return. Even if it hadn’t gone the way he’d hoped, at least Jack knew Dean liked him now. 

“Actually, I’m great.”

**Notes for the Chapter:**

> I have complicated feelings on Dean and Jack's relationship. Like, very complicated. But 15x14 really pushed me more to the positive side of that spectrum, and this was the result. As far as I'm concerned, as long as Dean continues to make an active effort and Jack wants to consider him a parental figure, I'll support it because Jack deserves all the happiness in the whole world. 
> 
> Thanks for reading!


	13. Breathe In, Breathe Out

**Summary for the Chapter:**

> Day 13: Oxygen Mask  
> Whumpee: Cas, with some Jack emotional whump for good measure  
> Set after 14x08, when Jack still has a soul but can use his powers. He's not supposed to, but he does anyway. Rebellious bean.  
> Also, this is kind of a loose interpretation of the prompt, but I think it turned out okay.

Dean really hated witches. Well, excepting Rowena. They’d been hunting one such non-Rowena witch, the four of them. And the witch was a real bad egg, going around and cursing kids for kicks. It’d taken them ages to track him down, but they finally did. He tried to throw a curse at Dean last minute, right as Sam got a witch-killing bullet fired off into his brain. But Cas, the self-sacrificing dumbass that he was, jumped in front of Dean, blocking the blast, and getting himself thrown into the wall.

Jack made it over there first, Dean just behind. Sam, lowering his gun, brought up the rear.

“Cas! Are you okay?” Jack was tugging on Cas’s arm, trying to pull him up. 

Sam and Dean just stared, searching for any sign of wear and tear on their friend. 

“I’m alright,” Cas grunted, sitting up. He spared a look of reassurance for Jack, and then turned to Sam and Dean. “I- it appears the curse has no effect on me.”

“So you’re okay?” Dean asked. 

“It seems that way,” Cas replied. Jack relaxed beside him, tension flowing out of his shoulders. 

Cas pushed himself up, everyone crowding around him to help. 

“How- you’re sure the curse didn’t do anything?” Sam glanced back over to the dead witch, nervously. “We could call Rowena, just in case.”

“Did anyone hear the spell?” 

They all looked at each other, helplessly. No one had. 

Sam gave a defeated nod. “Okay. I’ll look into it later, as long as you’re feeling okay.” 

Cas nodded. “I am.”

“Great!” Dean said. “Let’s clean up this mess and go get some food. I’m starving.”

\---------

They found a little diner, not too greasy, and sat down to eat. Dean forced Cas to get some fries, though he insisted he was fine and they should save the money, considering it wasn’t really theirs. 

“Appearances, Cas,” had been Dean’s reply. 

And so they’d ordered, burgers on one side of the table for Dean and Jack, a salad and a side of fries on the other. For the insane family members, who couldn’t appreciate the gritty, greasy flavor of crappy American food.

They’d all been in the midst of laughing when Cas had straightened, face falling. 

“Cas?” Sam asked, nudging him with his shoulder. 

Jack put his burger down, and Dean clenched his jaw. 

Cas didn’t respond, just shut his eyes and fell to the side, out of the booth and onto the floor. 

It didn’t exactly go unnoticed. Pandemonium erupted in the diner, a waiter dropping some plates. People gasped and chattered, some phones came out to record. Which was a surefire way to piss Dean off. 

Jack dropped down to his knees, face stricken, hands hovering over Cas’s body. Dean swept forward to pull him away, shielding the kid from the view of the other patrons. Last thing they needed was the kid on the internet. 

Sam knelt over Cas, taking a pulse and muttering faintly in Latin. Probably one of those healing spells he’d been working on with Rowena. Nothing happened, Cas still pale on the floor, and Sam looked over at them, eyes wide. 

_Shit._

They should have known they wouldn’t get a lucky break with that curse. 

The manager came over, saying she’d called 911 and an ambulance was on the way. Then she checked for a pulse, and immediately started doing CPR. Dean was a solid 80% sure Cas didn’t need to breathe, or pump blood, but that wasn’t a conversation he wanted to start. It was bad enough the hospital was gonna be involved- it would be easier if they could just take him back to the Bunker and call Rowena for help. 

Jack was staring at the scene, all big eyes and fear. Sam came over and led Jack away to sit down, an arm around him. Dean was left to field the questions.

————

Sam had known he should have done something more, been more adamant about checking Cas over. He’d been working with Rowena, he knew curses could operate on a delay. And could work on supernatural beings.

He didn’t have time to dwell on it now, though, because Jack wasn’t taking this well. Not that he should be expected to. Cas has told him Jack was a mess after Sam died, briefly, in the alternate universe. Looked like Jack wasn’t very good at processing loss, especially the three of them. Which they’d work on, given their dangerous lives, but it was okay. Jack was a child. 

So Sam led him away to an empty set of chairs, arm protectively around him. He glared at the people who stared, daring them to do anything. He got them settled, and turned to Jack.

“Hey, buddy. You alright?” 

“I- don’t know. What- I thought he was fine. I thought- I thought-“

“This isn’t your fault, Jack,” Sam soothed. “We’ll figure this out, okay? We always do.” 

Jack nodded, eyes trained on where the diner manager was still doing CPR.

Sam just squeezed his shoulder. If Jack didn’t want to talk right now, that was okay. Sam would just be here. 

———-

Jack decided he didn’t like hospitals. He barely remembered his time there, before he died, but they just smelled of fear and pain and sadness. He was also worried, and scared, and he could tell Sam and Dean were too. Cas getting taken to a hospital wasn’t a good thing, he knew that. Because it meant they’d have to be careful with their fake IDs, and because Cas wasn’t human. If the doctors found that out, it would be bad. 

They had to follow the ambulance in the Impala, and Jack was surprised and grateful when Sam sat in the back with him. It was nice to feel a steady presence next to him. 

Then they were herded to a waiting room, where Sam and Dean were bombarded with questions. Jack was sure they were spinning a good story, a sturdy web of lies. Jack didn’t like lying, and he hated when his family was hurt. He couldn’t think about losing them. He didn’t know what that would feel like, and he didn’t want to. 

So he sat, knees curled to his chest in an uncomfortable plastic chair. He only looked up when Sam’s hand hit his shoulder. Dean was leaning on the front desk, filling out paperwork.

“Jack?” Sam waited until Jack looked him in the eyes to keep talking. “You should try and get some rest. It looks like we’re gonna be here a while.” 

Jack just wanted to go home. But he nodded, shifting his legs so his feet were on the floor. Sam sat down beside him, one foot tapping anxiously. Jack let his head drop on the wall behind him. 

“I don’t like hospitals,” Jack muttered, closing his eyes. 

“Yeah, me neither.” 

And then there was silence, save for the beeping of equipment and the clacking of computer keys. He didn’t know how much time passed, until Sam was gently shaking his shoulder. 

“C’mon, Jack. They’re letting us in to see him.” 

They were led through a series of hallways and up some stairs, the doctor going on about a coma and how they needed to run more tests. Jack was barely paying attention, just focusing on walking. It was odd- he felt half-asleep, like he was in a daze. The doctor pushed open the door, and Jack shuffled in after Sam and Dean. When he looked up, he hadn’t known what to expect. 

It was jarring. 

There was Castiel, someone Jack had always known to be steadfast and full of calm, constant life, laying there like a rock. But inexplicably, what scared him the most was the oxygen mask attached to his face, the tubing that ran into his nose and mouth. It made him look weak, and that wasn’t a word Jack associated with any of his fathers. 

The door closed, making Jack jump. He realized the doctor had left, and Sam and Dean were watching him now with worry on their faces. 

“Kid? You okay?”

Jack nodded in Dean’s direction. “I- the mask. I don’t like it. It’s-”

“...gonna be off soon,” Dean finished. 

Jack blinked. What?

“I’ve been texting Rowena, about a counter-spell,” Sam said. “Turns out we had most of the ingredients in the car. We had to substitute one of them, so who knows if it’ll even work, but.. we have to try.”

“Yeah, especially before they call BS on that insurance information,” Dean grumbled, crossing to the other side of the hospital bed. 

“What can I do?” Jack asked, shifting forward. 

Sam and Dean exchanged looks. “We’ll let you know,” Dean said. 

Oh. That was code for telling him they didn’t need his help. If he had his powers, he could just fix everything and they wouldn’t be in this mess. 

Well. Technically, he could use his powers. But it would be dangerous. He watched as Sam and Dean did the spell, and waited a tense moment after. Nothing happened. The spell hadn’t worked. 

As Sam pulled out his phone again, to look for another solution, Jack decided it was worth the risk. He didn’t know how much longer he could stomach the worry, could take the sight of Castiel on the bed like he was broken. Not when Jack could fix it. 

He closed his eyes, ignoring the pull in his chest as he sent a wave of healing energy. Castiel opened his eyes a moment later, the room exhaling in relief. 

They had to call for a doctor to remove the breathing tubes, but Jack felt better. Despite the dizziness and the odd pit in his chest, he felt okay. He’d done a good thing. 

The Winchesters both clapped Cas on the shoulder, Dean telling him he shouldn’t go jumping in front of curses anymore. Jack was treated to a half-hug, Castiel smiling down at him. 

“Are you alright?” he asked. 

Jack paused. He thought so. “I think I’m just tired,” he said, eventually. 

All three of them frowned, but didn’t push it. Though Jack couldn’t quite shake the feeling that something _was_ wrong. With _him_. 

Once they were all in the car on the way home, that horrible oxygen mask long gone, the relief Jack felt wasn’t nearly as strong as he thought it should be.

**Notes for the Chapter:**

> Definitely didn't intend to get into any dark Soulless Jack there. Oopsies :)  
> Also, seeing a parent in the hospital hooked up to oxygen is pretty darn terrifying, for me at least. My mom had a big surgery a few years back and I remember being soooo freaked out by that mask. So, that's where that detail came from.
> 
> Hope you liked it! Comments truly make my day!


	14. Is Something Burning?

**Summary for the Chapter:**

> Day 14: Heat Exhaustion  
> Whumpee: Jack  
> No idea when this one is set. It doesn't reference any plot stuff, though, so it doesn't really matter :)

Neither Jack nor Castiel had any idea how to fix cars, which became evident when their truck broke down on the way back to the Bunker. They’d only been about eight minutes out from home, and Sam and Dean weren’t home to come fix it. They were about five hours away for a case, as a matter of fact. 

After a few minutes of staring at the engine and trying to puzzle out the owner’s manual, they decided to walk the rest of the way to the Bunker. It was hot, but the walk couldn’t take more than an hour and a half. And neither one of them was human; they could make it. Besides, they both liked nature. And though the side of the highway wasn’t exactly beautiful, it was kind of nice. 

With the truck safely tucked on the side of the road, Jack slung his backpack over his shoulder and set off next to Castiel. 

The sun was high in the sky without a cloud in sight, and as it beat down Jack started to sweat. He lasted about ten minutes before he swung his backpack around for a drink of water. 

And they walked on, Jack got warmer and warmer. He was fine though, they were almost there. And he was only half-human, he could make it. Cas, of course, was unbothered by the heat, even in all his layers. He noticed Jack wiping away at his sweat, and stopped walking. 

“Jack, let me take your jacket and your bag. I don’t want you to overheat.”

“I’m fine,” Jack said, but he acquiesced, passing the items over. It did feel better just in his t-shirt. 

“I think we should take a break for a while,” Cas said, starting over to a tree. Jack grabbed his arm and stopped him. 

“I’m _fine_ , Cas. I can make it. I just want to get home.”

Castiel didn’t look happy about it, but he nodded. “You tell me if you feel too warm, alright?”

“Okay.”

And so they kept walking, talking about random things, from the TV show Jack was currently watching to what they would do for dinner that night. In the silence between, Jack tried not to breathe too loudly. It felt like he couldn’t get enough air. He was still dripping sweat, and occasionally spots danced in his vision. He pressed on, focusing his thoughts on the cool air that awaited in the Bunker. And a long, cold drink of water. That sounded great. Sitting down sounded _really_ great. 

“Castiel? Can we slow down a little bit?” 

Cas looked at him in concern, immediately slowing his pace. “Of course. Are you sure you don’t need to rest?”

Jack nodded, blinking hard to dispel the spots. He was fine. He could do this. They continued at the slower pace, but Jack’s legs felt heavier and heavier. A few minutes later, he shivered, suddenly cold. He wrapped his arms around his middle, rubbing at them to get some warmth. 

“Are you cold?” Castiel’s voice sounded far away, hard to focus on. 

Jack just wanted to sit down. “Yes, but I can keep going-”

“No.” Cas led Jack, gently but firmly, further into the trees that lined the road. Jack half-walked, half-leaned on Cas, barely able to keep his eyes open. He focused on taking gulping breaths and riding out the sharp chills. Cas eased him down so he was sitting on the ground, leaning against a tree. 

He could feel Castiel’s fingers on his forehead, and he tried to squirm away, but Cas’s other hand held him gently in place. The chills vanished, but nothing else. 

Cold connected with his wrists, and he yelped in surprise. He looked to see Castiel’s fingertips on the underside of each wrist, his brow furrowed in concentration with his eyes shut. They stayed there for a few minutes before Cas gasped, the glow of his powers abruptly stopping. He took a heaving breath, nearly matching Jack’s, and then shifted to sit down next to him. 

“Are you okay?” Jack croaked.

“Don’t worry about me. Are you feeling any better?”

"A little bit. Not much." 

Cas pressed Jack’s water bottle into his hands, instructing him to take small sips of it. Jack obeyed. 

“What’s wrong with me?” he asked. 

“It’s heat exhaustion,” came the weary reply. “It happens when humans get too hot. I didn’t know it could happen to you. If I had, I’d never have- I’m so sorry, Jack.”

“It’s okay, Cas. I didn’t know it could happen to me either.” 

They sat in silence for a few minutes, watching the way the sunlight dappled through the tree leaves above their heads. Jack sipped his water, and Cas occasionally fiddled with his hands. 

“How close are we to the Bunker?” Jack asked, finally starting to feel cooler. Now he was just tired, but he’d rather be tired at home. Even though it was a pretty spot they’d found to rest in. 

“Just a few minutes, I think,” Cas said. “Do you feel strong enough?” 

Jack took a deep breath. “I think so.” 

Cas helped him to his feet, and they continued their walk, slow and steady, Jack leaning on Cas when he needed to. 

They reached home, finally, and Cas instructed Jack to drink more water and eat something, cooling down a while longer before he surrounded himself with steam from the shower. 

When Jack laid down to sleep that night, bone-tired from the day, he decided he never wanted to experience heat exhaustion again.

**Notes for the Chapter:**

> I struggled with coming up with a situation where one of them could even get heat exhaustion, so I hope this chapter was okay! Thanks for reading :)
> 
> And pro tip from someone who has had heat exhaustion multiple times (because I'm kind of a dumbass): If you have access to ice cubes, putting them on the insides of your wrists and/or the back of your neck actually works to cool you down. Also, you gotta make sure you're steady and cooled off enough before you do something that surrounds your body with an extreme temperature, like showering, otherwise you'll just shock your system and possibly make it worse. I've given myself heat exhaustion from showering in water that was too hot (I was 12. It was a wild time). And shivering in 99 degree weather (Fahrenheit) is one of the scariest things I've ever experienced. 
> 
> Anyway, if you feel yourself start to overheat and are in a position to rest/get to shade- please do it. Don't be dumb like me and push until you almost faint. Stay safe in hot weather!


	15. Into the Unknown

**Summary for the Chapter:**

> Day 15: Possession  
> Whumpee: Sam  
> Set immediately following 9x11- Gadreel fallout.  
> WARNINGS:  
> This chapter is NOT Dean-friendly. At all. So if that is going to stress you out or make you mad, please skip this one.   
> Also, it's very dark. Since possession on the show is a rape metaphor, it's also one here. If that is triggering for you, at all, please be careful. If this were a standalone story, it would have the rape/non-con warning on it. Stay safe.

Sam sat on the edge of his bed, staring into space in the general direction of the door to his bedroom. 

It’d been about a week since… 

Well. 

Cas had lingered for a while, helping as best as he could. Sam appreciated it, more than he thought Cas would ever realize. It was nice to know he still had someone he could trust. 

Though Dean was the one he was supposedly always able to count on. Ha. 

No, really. _Ha._

It’s funny. It’s funny how for thirty-odd years, Dean Winchester swore up and down that he’d look out for Sam, come rain or shine, death or Hell, whatever. And then he turned around and let him get possessed. 

Good God. 

The most terrifying thing, Sam mused to his lonely little wall, was that it wasn’t the first time. Sam was good at finding patterns. It was kind of in his job description. So when he started to see connections, he couldn’t just _unsee_ them.

He had to fight not to get bogged down. Because thinking about this brought on thoughts of a bucket in the panic room, of many a punch in the face, of poor, innocent Amy, of _if I didn’t know you I would wanna hunt you_ and a vague, dusted memory deep in the shelves of his mind. Of Dean beating his body senseless, till he passed out, because he hadn’t been acting like himself. 

And he wasn’t, at the time. Not really. He’d been soulless. But Dean just up and decided that if Sam wasn’t Sam enough for him, he could hurt him?

Who gave him the right? _Who gave him the fucking right?_

The first time he’d been possessed, Meg parading him around on murder sprees, nearly making him rape Jo- Dean had punched Sam for his trouble. 

Sam had been kidnapped more times than he could count. He’d been poked and prodded by all kinds of monsters, some human. 

Like Becky. She wasn’t a monster by any means. Sam thought she was probably a fine person, if overly obsessed, not that he ever wanted to be in a room with her again. He’d been uncomfortable enough with the groping. Next thing he knows, he’s tied to a bed with his pants gone. And Becky’s there, all touchy-feely and agonizing over how her shitty decision to _drug him_ wound up backfiring on _her_.

Again, funny. Because that’s probably what Dean was doing this very minute. 

Oh, yeah. Right about now Dean would be three bottles deep into some unlucky bar’s supply. He’d be feeling all sorry for himself because- surprise of all surprises- lying to Sam for months after tricking him into consenting to a possession _fucking pissed Sam off._

And then, because his life sucked triple that, Sam felt guilty. He felt bad about feeling bad, and that was about three tons of fucked up that he didn’t want to begin unpacking. 

Cas. Cas had hinted at encouraging a reconnecting with Dean, for logistical Abbadon-and-Metatron-fighting purposes at the very least, but he didn’t push. That was trust. That was- that was _respect_. Respect for Sam’s choices and Sam’s autonomy. 

Truly, what a concept. 

Sam figured, after this shitstorm, he could always count on Cas, but that didn’t mean he wanted to shove all his issues on him. His friend had enough to deal with on his own. 

Dean, though… Sam didn’t know if he could trust him. Ever again. 

Sam could say for certain he would never allow Dean to get possessed. He didn’t have it in him to put anyone else through that, least of all his brother. Even without the first-hand experience, they’d seen enough vessel horror stories to know it was a bad idea. 

Meg Masters. Jimmy Novak. Ruby’s vessels. One of Raphael’s had quite literally been reduced to a slobbering mess. And Lucifer’s-

_Stop._

It wasn’t as if Dean was a stranger to any of this. He’d been under pressure to say yes to Michael, and he hadn’t. Because it was his goddamn choice to make. What about that was so hard to understand?

Sam just didn’t get it. Plainly didn’t understand. Didn’t get how Dean possibly had this in him, was capable of such a disgusting thing. He may as well have sat and watched someone rape Sam while he was unconscious, all the while saying, “oh, yeah, go ahead. As long as you, a total stranger, pinky promise that everything will work out.”

Sam loved Dean. He’d never stop as long as he lived. Even after. Even in Hell. But right now, when the lines between “saving” and “cursing” and “condemning” and “family” blurred into a great big ugly mess, where autonomy and choice weren’t even in the same ballpark, Sam couldn’t trust him. 

Dean didn’t respect him. He’d proven that. Castiel did, Dean didn’t. Seemed like that should feel odd, should feel all screwy and off-balance. 

It didn’t. 

Sam stood up in a rush, digging his nails into his palms. He needed to do something. Needed a case. He picked up his phone from the bedside table, seeing a text from Cas and a news notification. 

Cas had sent, “How are you feeling this morning?” followed by a dorky little sun emoji. It should make Sam smile, maybe even laugh. Any other time, it probably would have. 

Now, all he could do was type back an “I’ve been better.” 

He opened the news app, looking for accidents and brutal murders. Anything was better than sitting here, lamenting broken brotherhood. 

Dean made his choice, and for once Sam wanted to make him deal with the consequences, face what he’d done and make him understand it if it took beating his skull in with a stick. 

Sam didn’t do those kinds of things, though. He couldn’t, because nearly everything under the sun had been done to him and he was powerless to stop it. 

_Focus, Sam. Find a case._

Sam had work to do.

**Notes for the Chapter:**

> I'm still upset at Dean for season 9. Like I love him, I do, but that was absolutely deplorable.
> 
> Thank you for reading! I'd love to hear what you thought.


	16. A Terrible, Horrible, No Good, Very Bad Day

**Summary for the Chapter:**

> Day 16: Hallucinations  
> Whumpee: Sam  
> Not set anywhere specific, but it references a lot of things. This one is also very dark, so read carefully.

Bad days weren’t all that common, not anymore. “Bad” being a relative term. “Bad” meaning anything from “I can see shadows where there’s nothing there” to “Lucifer’s laughing at me as he paints the walls with my blood.”

Most days he was fine. “Fine” was a relative term too, of course. And a lie more often than not. Still, if Sam managed a few hours of sleep, got some exercise, and nothing too extremely terrible had happened recently, he might be fine. 

Sometimes, though. Sometimes Dean’s smile would flicker into something twisted, and Sam had to fight not to jump as Dean’s arm swung a hammer at his head. 

_Not real not real not real._

One time he’d caught Cas in the library, trench coat uncharacteristically off. Sam had staggered back before Cas could notice him, as his mind replayed that arm ripping at his soul, the Devil looking at him through those eyes. 

_I will touch your soul, since you asked so nicely._

Sam rubbed at his palm, eyes squeezed shut. Told himself that was over, it was just Cas in there, not Lucifer- and tried to breathe steady. He couldn’t. When he opened his eyes, he saw blood dripping from the walls. Inexplicably, but it was there. And phantom memories followed for the rest of the day.

_Not real not real not real._

She looked like Ruby. Not really. The cheekbones weren’t sharp enough, the hair too long. But enough. 

She was an innocent, someone they needed to save. Sam couldn’t look at her. 

He tried, and all he saw was Ruby, looking at him like he was a savior for dooming the world. 

_You never needed the feather to fly, you had it in you the whole time, Dumbo!_

Sam pretended he couldn’t hear his heart pumping, a familiar hunger buzzing under his skin. He pretended he didn’t imagine neat cuts on the girl’s arms, pretended he didn’t feel the urge to reach over and grab her by the wrist and _drink_.

_Not real not real not real._

He walked into the kitchen to find Dean chopping up meat for dinner, bopping along to the music in his headphones.

He pretended the knife didn’t flicker to look like the First Blade, that he couldn’t see the Mark burning and burning and burning on Dean’s arm. 

_Not real not real not real._

Jack’s eyes glowed yellow, and Sam didn’t see Azazel’s grin. 

_Not real not real not real._

Most nights he slept on his stomach, or at least started that way, so he wouldn’t have to open his eyes and see Jess burning on the ceiling. 

That couldn’t stop him from feeling phantom hands trailing over his body, Lucifer’s voice next to his ear. 

_Not real not real not real._

Bad days, truly bad days, with maggots in his food and fires everywhere and hooks in his skin and blood, blood, blood… those were rare. But the flickers, the cracks, they were always there. 

He’d hear Heat of the Moment in total silence. He’d see faces screaming from the walls, of people he’d failed. He’d look at Dean and Cas and see the times they’d been twisted and other, just ghostly memories juxtaposed to the present reality. But what was reality, really, to someone whose mind was so jumbled?

So he ran. He ate, carefully. He read books and worked and spent time with his family in the moments between disasters. 

And he made sure they never saw the way his fingers still dug into his palm. 

Because the wall in his mind had fallen long ago, leaving Sam like Atlas, holding everything on his own two shoulders. Feeling the strain every second. 

He couldn’t let go, couldn’t stop pushing against it. Because if he did, even for a second, then he’d truly be broken.

**Notes for the Chapter:**

> Where did the overall fandom get the idea that Sam is calm and collected? He comes off that way deliberately to other people but like... that man is two seconds from snapping. His strength is insane. And I love him a lot.   
> Also, a little detail that makes me endlessly sad is that if you watch really carefully, you can see Sam doing the hand thing beyond season 7. I just wanna give him a hug.
> 
> Thanks for reading! Reviews are literal day makers :)


	17. I Did Not See That Coming

**Summary for the Chapter:**

> Day 17: Dirty Secret  
> Whumpee: Everyone? Yeah.  
> SPOILER WARNING for 15x15. If you're not caught up, please do not read this. Please. I loved the ep, even if it emotionally devastated me, but I would absolutely hate to spoil any of y'all. In case people skim over these, let me repeat myself:  
> 15x15 SPOILER WARNING  
> 15x15 SPOILER WARNING  
> 15x15 SPOILER WARNING  
> Whew. Okay. If you're caught up, enjoy!

Winchesters dealt in secrets like gas stations dealt in cigarettes and lottery cards. 

Dean and John kept the truth about monsters from Sam until one fateful Christmas when their carefully sculpted lies and omissions and half-truths came crashing down. 

\---------

Sam applied to college without breathing a word.

\---------

John didn’t find out that Sam had demon blood, not in so many words. But he’d been tracking down a rare demon, one he thought was a lead on what killed Mary. He got it tied down in a trap he’d seen in one of Bobby’s books, and was in the midst of the exorcism when it looked up at him, eyes black in the pretty face of it’s stolen body.

“Send me back, fine. But the Boy King is here. And nothing you can do will stop him from fulfilling his destiny.”

John pieced it together over time, that his little boy was the Boy King of Hell. And he took it to his grave.

\---------

Dean kept John’s last words inside until he couldn't anymore, and then everything was just a great big mess. He couldn’t tell if he wished he’d told the truth from the start or never told Sam at all.

\---------

Sam asked, “Did I die?” and Dean had to tell him the truth. He’d give anything to keep the lie, because the look in Sam’s eyes was awful. And it stayed around for the whole year, until Dean died in a bloody, gory blaze. Probably best that secret hadn’t been kept, or the look in Sam’s eyes then, as he watched Dean get ripped apart, would have been a thousand times worse.

\---------

Castiel fought his way into Hell and out to save Sam Winchester, but something was wrong. He knew something was wrong, but he couldn’t figure out what it was. And then he was in the thick of the mess with Raphael and Crowley and averting the second Apocalypse. He heard Sam’s questions, tentative prayers sent up, gradually angrier as Castiel neglected to appear. He couldn’t go down there, because if Sam asked him directly how he got out of Hell, Castiel wouldn’t be able to lie to him. And though he didn’t quite know why, he knew he didn’t want Sam to know. 

So he kept it a secret, even implied he didn’t care about Sam as much as Dean. Another lie to add to his ever-growing convoluted web. And when the truth came out over a ring of holy fire, many months later, Castiel couldn’t help but wonder what would have changed, if this could all have been avoided if he’d only answered that first prayer a year ago. 

\---------

Sam was fine. He coughed up blood, far too much blood to be safe, but he was fine. There was no need to tell Dean about it, he was mother-henning enough as is. 

There also wasn’t any need to mention how his vision sometimes whited out, or his ears rang or his hands shook or any number of other abnormal things running wild in his body along with the ever present fever. The Trials hurt, bad, but they were purifying him. They’d be worth it. 

Sam was fine, so he kept his lips sealed. Until it all came spilling out in a church, when he let it all go and collapsed into his brother’s arms. 

\---------

There was a time where Sam struggled with lying to Dean. As a kid, it was because Dean could see right through it, having taught him all the tricks. Sometimes it was because Dean just knew him too damn well. Having grown apart these last few years, though- it was scary how easy it was to skulk around behind his back to look for a way to get the Mark off. 

Not as scary as the consequences if he didn’t find it, though, so he kept looking. Including clandestine phone calls to Cas and Charlie. The whole deal. 

Not a word got out until it was too late.

\----------

Jack had never really kept a secret before. Not one this important. 

It crossed his mind that maybe he should tell Sam and Dean what had happened, because they could help fix it. But Cas was right, they’d be worried, and Jack didn’t want them to worry. 

That didn’t stop Jack from worrying about Cas, though. 

Jack also didn’t want Cas to be mad at him. He’d asked him not to tell, and Jack wanted to respect his wishes. He’d made the deal for him, so wasn’t doing what Cas asked of him the least he could do? 

Jack kept his mouth shut. It wasn’t lying if no one asked. And as his soul burned away, the worries whittled down too.

\----------

Dean mentally kicked himself. He’d been an idiot, giving in to the urge to hug Sam goodbye. He’d figure out something was up and be on Dean’s ass about it before he could blink. 

Nothing to do but keep up his little farewell tour and get to welding that goddamn box. If his secret wasn’t gonna last for long, he’d better get going.

\---------

Driving back to the Bunker was surreal. Cas fought to keep the steering wheel steady, to keep his eyes dry. He resisted the temptation to pull over and do… something. Yell or simply pull Jack to him and never let go, he didn’t know. 

He’d verbalized for the first time what Jack truly meant to him, and it didn’t begin to scratch the surface. He would not- could not- watch Jack die another time. He refused. He didn’t care what it took, if he went down trying, he would not lose his son again. 

Jack had sounded close to tears, sounded like he was putting on a brave front. And he was so, so, brave, truly- but this was more of a burden than anyone should ever have on their shoulders. 

_I’m gonna die._

No. No. Jack couldn’t. Cas wouldn't let him, never again. And if he had to tell Sam and Dean, against Jack’s wishes, in order to accomplish that? Then secrets be damned. 

There’d been too many over the years in their family. No more. 

Not when the stakes were this high.

**Notes for the Chapter:**

> I know I didn't get every secret, but come on- we'd be here all day if I had.
> 
> Thanks for reading! I'd love to know what you thought!


	18. Panic! At the Disco

**Summary for the Chapter:**

> Day 18: Panic Attack  
> Whumpee: Jack  
> Set between 15x13 and 15x14.

After Jack got his soul back, everything hurt. Sam and Dean’s silence felt like a knife to his heart, and after a while he ran past them to his room and shut the door. He curled up on his bed, arms hugging his legs, his face pressed into his knees. He didn’t know how long he stayed there, mind whirling and his stomach burning with the force of his guilt. He’d loved Mary, and he’d killed her. And in doing so, he’d taken from Sam and Dean a mother. While Jack was still missing his every single day. 

What would his mother think of him now? What did his fathers think of him now?

Eventually there was a knock at the door, and Castiel’s voice came through. “Jack?”

Jack didn’t say anything, couldn’t. A fresh wave of tears came on, and Jack just tried to breathe. He didn’t want Cas to come in and try to comfort him, though it was what he wanted. To be safe and start to feel like it was okay again. But he didn’t deserve that, didn’t deserve comfort after what he’d done. It was a selfish, childish want. Jack had never had time for those, he couldn’t start now.

“Jack,” Cas repeated, and Jack could imagine the look on his face. Sad and sympathetic and everything Jack didn’t deserve to have directed at him. “Jack, may I come in?”

Jack stayed quiet. Quiet enough to hear Castiel’s sigh through the door. 

“Okay,” he said. “Okay. I’ll just- I’ll just go then.” 

Jack didn’t want him to. He didn’t. He’d blurted out “wait” before he could stop himself. 

He knew Cas was waiting for permission to come in, so he gave it. So quietly and so faintly that he wasn’t sure it would be heard at all. But the door pushed open, and Cas slipped in, closing it behind him. Jack looked up, heart clenching at all the love and concern he saw. He didn’t _deserve_ it. He didn’t. 

“Oh, Jack.” And Castiel was moving towards him, to hug him or to put a hand on his shoulder Jack didn’t know, but it was comfort he shouldn’t be allowed to feel. Parental comfort he’d taken from Sam and Dean forever.

“Don’t,” he choked out, scooting away, and Cas dropped his arms. 

Hurt flashed across his face, and now Jack was just feeling more guilt. Nevertheless, Cas nodded and perched on the edge of the bed, hand close to Jack’s foot. Jack put his head back down, but he could still feel Castiel’s presence. His eyes on him. 

Jack was swimming in his guilt. 

It was a long time before Cas spoke again. 

“I- Sam and Dean believe that we should start looking for Amara. I’m going to go out, ask a few angels if they have any leads on her location.”

Jack looked up at that, his eyes stiff from so long crying and then so long screwed shut. Cas was leaving?

He looked sad about it, but Jack knew that finding Amara was necessary. Cas was waiting for a response, and so Jack nodded. Cas nodded back, standing up and heading to the door. He paused, turning back to where Jack still sat on top of his blankets. 

“You should get some rest,” he said. “Try laying down, shutting your eyes.” 

Jack didn’t have the energy to fight that, didn’t want to see more pain written out on Castiel’s face. So he obeyed, slipping under his blankets. 

“I’ll see you soon, Jack,” Cas said, flicking off the lights as he softly shut the door. 

Jack’s breath caught. He didn’t know why, it wasn’t like Cas or Sam or even Dean had never done that before. But now, in the sudden darkness, he felt like he couldn’t breathe. 

It was fear, and so much of it at once. He felt wrong, wrong, _wrong_ , like there was water over his head and he couldn’t make it up for air. His heart was beating far too fast, his mind spinning on a memory, on thoughts he couldn't stop. 

The Empty. Dark, alone, dead. Knowing he should be feeling _something_ about what had happened. Knowing he should feel scared, because this place scared Castiel and he didn’t scare easily. And then the entity was there, that oozing mess of darkness and power, and Jack felt nothing. He knew he should fear it, hate it for hurting his mother and preventing one of his fathers from ever being happy, but he felt nothing. And then Death came and put the weight of the world on his shoulders. 

Jack wanted to scream. It was all too much, but somehow he made his body move, scrambling up to turn the light back on. It flooded the room, making his eyes hurt, but it was better than the all-encompassing darkness that crawled its way under his skin. 

He leaned on the wall, bonelessly, taking heaving breaths. He felt drained, and so very tired. But he couldn’t turn the light back off to go to sleep.

When he could barely stand anymore, he stumbled into bed, lights on, and slept an uneasy, guilt-ridden sleep.

\----------

When he woke up, he was hungry. He didn’t want to go to the kitchen, though, since Sam or Dean might be in there. He couldn’t face them.

So he just laid there, a few more hours slipping by in a blur along with some tears. 

“Jack?” Sam’s voice and accompanying knock were soft, and so gentle that he thought he’d imagined it. 

“Hey, bud. It’s okay if you don’t want to come out yet, so I, uh, I brought you some food.”

Sam waited for a response, but Jack stayed silent. Maybe Sam would think he was asleep, and go away. He shouldn’t be wasting his time on a murderer, no matter how much Jack wanted to open the door and bury himself in Sam’s arms where he could feel safe, and understood, and for just one little moment forget about all of his responsibilities. 

“I also- uh. I noticed you kept your light on last night. And I brought you something for that too, just in case you want it.”

Jack frowned. What could that be? 

Sam waited a little longer. “Okay. Okay. I’m just going to leave the food here, okay? Come get it when you’re ready.”

It sounded like Sam wanted to say something else, but after yet another long pause Jack could hear his footsteps trailing away. Jack stood up, feeling a little woozy, and made his way over to the door. He cracked it open, seeing the bottle of water and a bowl of his favorite cereal. Sam normally didn’t want him eating that. He always said it was bad for Jack’s teeth. Next to the bowl was a little light bulb, unlike anything Jack had seen before. He took the items into his room, setting the cereal and water down on his table. He found an outlet and plugged in the lightbulb. 

It cast a small, warm glow a few feet around. Jack got up, turning off the main light. 

With the light Sam had given him on, the room didn’t feel like the Empty at all. And the glow reminded him of the Impala’s headlights. It was safety. It was Sam, and it was Dean. It was like the shimmer of Castiel's grace when he healed someone. It was home, in a color and a feeling. It was Mary's smile. 

It hurt as much as it helped, that light. But it was easier to sleep that way. And maybe, sometime soon, it wouldn't hurt so much at all.

**Notes for the Chapter:**

> I feel like a lot of these are very loose interpretations of the prompt, or it's a very small part of the actual chapter. Oops? I hope y'all don't mind. 
> 
> As usual, thanks for reading! You readers are the best.


	19. Broken Hearts

**Summary for the Chapter:**

> Day 19: Survivor's Guilt  
> Whumpee: Castiel  
> References a lot of things, but I guess it would be set in that mountain of untapped Cas angst between 15x03 and 15x06. I say untapped, but this is the second chapter in this fic alone where I'm addressing it. Oops?  
> This also gets very dark, so proceed with caution. Lots of intense Cas self-loathing ahead.

If someone were to ask Castiel what his biggest regret was- well. He had a long list. 

He could tell you about releasing the Leviathans, nearly causing another apocalypse. And that was only after declaring himself God in a fit of ego and warped morality. 

Or, he could tell you about consenting to Satanic possession, which caused many, many deaths and an abundance of chaos. 

He could tell you about killing his brother Balthazar, his closest friend for ages, in a moment of weakness yet again brought on by overinflated confidence. He could tell you about all the terrible things he had done, the means to justify the end, not the least of which condemning one of his chosen family to remembering centuries of torture in Hell, when Castiel had failed to save him from it in the first place. 

He could tell you about a boy, a child he swore to protect. A child who died painfully not once but twice under Castiel’s supposed protection. A boy who was constantly battered, bruised, and hurt because Castiel was not a worthy guardian. 

A boy whose corpse he had destroyed to kill the thing that walked around in it, that dared to wear his face and walk with his legs and speak with his tongue. 

Those things, though they made Castiel _ache_ with guilt each time he thought of them, were not his greatest regret, his biggest mistake. No, that was one that he wore quite literally each and every day.

Jimmy Novak.

He’d thought he understood how wrong it was, but he hadn’t. Not for a long time. When Jimmy died, went to rest in Heaven, Castiel had thought it was fine. He did feel some remorse about having cut Jimmy's life short, but it was surely much better in paradise than on earth, where each human seemed to be tortured by the trials of everyday life. 

Cas hadn’t yet realized that he was the monster. 

When Castiel was human, he hadn’t given a thought to the person who once resided in the body he was now trapped in. It was a blink of an eye for an angel, the few years that Jimmy had been dead, but so much could happen in a few short years. He knew that now. 

Meeting Claire the next year forced him to confront that guilt. He had to face the fact that nothing he could ever do would make it better, could fix his worst mistake. Claire was kind, if troubled, but it wasn’t as if Castiel was unused to that. He did consider Winchesters family, after all. 

Claire should hate him. She did, somewhat, but she also gave him a chance. A chance that he most certainly did not deserve. Cas vowed to look after her as best he could, feeling he owed it to Jimmy. The man from whom Cas had first learned what it meant to be human, to love family above all else.

But he still hadn’t understood, not fully. 

Knowing Claire made Castiel cognizant of his stolen body, every second that he wore it. Sam and Dean seemed to forget. 

And then Castiel was possessed by the Devil. His own doing, of course, because he could never seem to do anything right. And Sam got hurt because of it, both Winchesters were betrayed because of it, and Castiel thought he could understand a little bit better just how awful it must have been for Jimmy in those years. Castiel had tried to shield him, of course, spoken to him a few times. But it was still a violation of the worst kind, no matter if consent was given.

He could never make things right with Jimmy, so he tried to help Sam, to relate to him through their shared experience. Maybe it would remind him that Cas was there, that he would be there to listen if Sam was ready to talk.

For all that Castiel chose his words with care, they were wrong. He had messed that up, like everything else he ever attempted. 

Because how could the violator ever think he could relate to the violated?

Jack changed everything. Here was a bright, bright soul, so young and innocent and full of life. And he trusted Castiel to keep him safe. 

In Jack, Castiel had a son. And it was only then that he realized he hadn’t done Jimmy any favors by sending him to paradise early. In fact, he’d committed an atrocity.

Because he knew, now, that all the pain of life, all the tragedy and all the struggle, was worth it if he could make his child smile. That every moment with Jack was a gift, a blessing. One he in no way deserved, since he had stolen those moments with Claire from Jimmy. Stolen them just like his life and body. 

And watching Belphegor saunter around while wearing Jack like a coat, Castiel wondered how Claire had ever managed to even be in the same room as him. Because he knew now that just because a vessel was empty, its soul moved on, it was still a deplorable, wretched, and terrible thing to parade around in it as your own. It was the worst kind of disrespect to their memory. 

If anyone deserved to be here now, it was Jack. And it was Jimmy. Not Castiel. 

He’d failed everything he’d ever attempted, hurt everyone he’d ever loved, and stolen an innocent, kind man’s life. Beyond that, he’d stolen a father from a daughter and a daughter from a father. 

Castiel loved Jack _fiercely_. Looking at him, Castiel saw all the good in the world, maybe even thought that there could be some good in him as well, if someone as kind and pure and truly wonderful as Jack could love him and admire him. 

Castiel loved Jack, missed him even more. But for all he’d found himself in fatherhood, he’d also uncovered new oceans of guilt to drown in. He could fight it while Jack was around, because he would fight the fabric of the very universe for him. But now, with Jack gone and a jagged chasm between him and the Winchesters? 

Well, Castiel was tempted to stop swimming at all. Sink right to the bottom of those oceans of guilt until he could feel nothing but the Empty's cold, unforgiving grasp. Nothing less than he deserved. 

He didn’t stop fighting. Because there was a part of him that knew Jack’s story couldn’t be over, yes- but also because it would be a disservice to Jimmy to do so. To give up, when Jimmy had lost so much for Cas to even exist on this plane. 

So Castiel would keep living. He had to.

But wearing the reminder of the life he'd taken, seeing it in every reflective surface he passed- in those moments, he would always choke a little more on the guilt. 

Always remember that he was the one who deserved to be dead.

**Notes for the Chapter:**

> Just to be clear, I 100% do not believe this. I do believe that Cas thinks about Jimmy a lot, though, especially since he's a dad now. And we all know that Cas's self loathing knows no bounds, a fact which makes me endlessly sad. I want someone to tell Cas that they love him in the last few episodes (hopefully Jack) so that maybe Cas can finally see the good he's done, the positive impact he's made. I feel like just having Jack is a step for him, honestly, but loving yourself is always a difficult thing to do. 
> 
> Sorry, this is a long note. I just have a lot of feelings about Cas (if y'all couldn't already tell). 
> 
> Comments are appreciated!
> 
> Also, I realized I really haven't been whumping Sam and Dean that much in this. Don't worry, though, they're getting hit tomorrow :)


	20. Toto, I Have a Feeling We're Not in Kansas Anymore

**Summary for the Chapter:**

> Day 20: Field Medicine  
> Whumpee: Dean (and Sam)  
> Set pre-series! Sam's 14, Dean's 18. Medical inaccuracies abound.

Hunting with all three Winchesters was always an ordeal. Not just because that meant Sam and Dad were always at each other’s throats, but also because Dad had a habit of making them split up, leaving Dean with Sam’s constant griping. Sam would be good at the job if he’d just accept that it was what they had to do and stop whining about it. He was fourteen, God’s sake, he could handle a gun just fine.

Besides, Dean would be right there. It wasn’t like anything would happen to him. 

He really should have thought about what it would be like if something happened to _Dean_.

The bullet came out of nowhere. Maybe it was the crazy old farmer who they hadn’t realized was still home. Maybe one of their bullets ricocheted. It didn’t really matter where the bullet came from, but it was now lodged in Dean’s stomach. And he went down, hearing Sam’s shout from next to him, seeing the panic flash in his eyes. 

“Dean!” 

Sam skidded down next to him, eyes wide. “Oh my god, Dean, are you- are you-”

“Is there an exit wound?” Dean ground out, teeth clenched. This damn bullet _hurt_. He’d been skimmed before, but he didn’t think he’d been full on shot-in-the-stomach shot before. 

Sam was babbling. “I don’t- no, there’s not. There’s not. I don’t- Dad! Dad, help! Dad!”

Dad was gonna be too far to hear that. They were by the car though, so Dad would eventually come back this way. So all they needed to do now was keep Dean from bleeding out. 

“Sammy, he’s too far.”

Sam looked back at him through all that shaggy hair. Needed a damn haircut, like Dad was always saying. 

“I don’t know what to do, Dean. There’s a lot of blood, do I push on it?”

Dean made a strangled sound, stopping Sam’s hands a few inches above his stomach. Dean could feel sweat beading on his forehead, feel the muscles cramping where he was craning his neck to keep looking at Sam.

“You gotta take the bullet out.” He knew that was the next step for sure. Couldn’t leave metal inside him, right? Didn’t know where it’d been. 

“I- now? You need a hospital, Dean. I mean, this isn’t sanitary, and I’m not a surgeon...” Sam’s voice was intense, but still quiet and subdued. 

“You gotta take the bullet out, Sam,” Dean repeated. “Get the kit, get the whiskey, and get your ass back here.”

Sam was shaking his head. “I’m not gonna- no. You need a hospital. I can drive you, we just have to get you into the car…”

“And leave Dad? We’re not going anywhere, Sam.” Dean grit his teeth against another wave of pain. “Just take the damn bullet out, okay? This stuff comes with being a hunter.”

Sam’s face changed, twisting up into something unreadable. Apparently the worry for Dean’s immediate safety won out over whatever else was going on in that big brain of his, and Sam scurried into the Impala, coming back with the medical kit and a bottle of whiskey. 

Dean took a great big gulp, passing the bottle back to Sam. 

“Alright. Pour me one.”

Sam did, jaw clenched as Dean grunted at the burn of the alcohol on his open wound. When it subsided, the spots receding from Dean's vision, Sam already had the bottle capped and put to the side, and a pair of tweezers in hand. 

“Okay, I’m ready,” Dean said, clenching his fists. The whiskey he’d drank was starting to kick in. He’d be fine. 

“I’m not,” Sam grumbled. But he took to the wound like a pro, digging the bullet out carefully and precisely. 

“Looks like dissecting those frogs in school is finally good for something, right Sammy?”

Sam glared at him and dumped more whiskey on the wound. Dean grimaced, throwing his head back where it knocked on the hard-packed dirt.

“Warn a guy next time, would ya?”

“Oh, I’m sorry. I just thought you’d prefer to not get an infection from surgery on the dirty ground.” 

“Just stitch me up and quit whining.”

Through the buzzing of the whiskey Dean barely felt the needle. It was more of a tickling pin-prick than a stab and pull. 

“Done.” Sam pulled out gauze and pressed it gently to the top of the stitches, sealing it down.

“See? Just like a champ.” Dean grinned. Sam glared.

“This isn’t a good thing, Dean,” Sam said, voice rising in anger. “You got shot, and I’m the one who had to stitch you up! This is messed up. We shouldn’t have to live like this.”

Dad wouldn't like hearing that tone. “Sam, it’s the life. This is what we do. And it’s fine, I’m fine, you’re fine. We’re all gonna be fine.” 

His speech was only slightly slurred. Sam sighed, long and tired, and scooted over to sit next to where Dean was all sprawled out, pulling his knees into his chest. 

“Right. We’re all gonna be fine.”

They sat in silence for a few minutes, waiting for Dad. Dean watched the stars and Sam stared at the grass. It was kinda nice, if he ignored the fact that he’d just been shot and had his little brother playing field medic. It _was_ messed up, but it wasn’t like there was anything to do about it. They were Winchesters.

This was their life. 

“Hey, Sam?”

“Yeah?” 

“Thanks, bitch.”

Sam snorted, picking absently at a blade of grass by his shoe. 

“Yeah, okay. You’re welcome, Jerk.” 

Dean was glad it was dark, because he’d never admit to smiling.

**Notes for the Chapter:**

> I feel like the boys bickered ALL THE TIME as teenagers. And I also think they knew how to stitch up wounds at young ages. This chapter was my attempt at combining those two things. Did it work? Let me know!
> 
> Thanks for reading!


	21. I Don't Feel so Well

**Summary for the Chapter:**

> Day 21: Chronic Pain  
> Whumpee: TFW 2.0  
> Set in an ambiguous season 15-ish zone. It doesn't really matter, it mostly references other events.

Dean wasn’t 26 anymore. It sucked. He had achy knees and an achy back, which was not conducive to long drives and constant drinking and his general lifestyle.

The more terrifying, constant aches- those were different. Sometimes his forearm still burned, making his heart pound and the blood rush in his ears, his fingers itch for the first blade. 

He ignored it, most of the time. But the hot flares of anger, those were harder to avoid. It was like hellfire scorching its way up his throat and out before he could take the words back. 

Anger used to be a defense mechanism, a false front. 

_I’m 90% crap._

Now the anger was all he had left, always burning. Always scraping more shards off his broken soul and painting them black.

\------------

Sam got headaches. Which wasn’t new, he’d always been a headache-y kind of person since he was a kid. But sometimes he could swear his headaches were more like what he’d had when he was having psychic visions, all those years ago. Sometimes he thought he could see faint impressions of people on the backs of his eyelids, people he would run to save if only he could just _see_ them.

But he wasn’t still having visions. Couldn’t be. It was just a trick of the light from his never-ending headaches. 

Right?

\------------

Castiel tried not to think about it, but he was in pain nearly every minute of every day. His wings- they were mangled and broken, his feathers twisted and bent over in places that were meant to be inflexible. Not to mention the hellfire scars, the way they sometimes still flashed with phantom burns. 

At least his family couldn’t see the way his wings lay crooked and folded in, dragged behind him when he walked. They’d be disgusted, and that might hurt worse.

\------------

Jack’s heart ached. Always.

There was always something to be sad about- his mother, the people he’d lost, the way his fathers dragged their feet and ducked their heads with the light dimmed in their eyes day after day. 

Sometimes, as he sat in the dark trying to fight off the nightmares enough to sleep, he ached for himself. For the childhood he’d never have. 

It was an ache that would never get better.

**Notes for the Chapter:**

> Short and hopefully not sweet. Hope y'all enjoyed!


	22. Do These Tacos Taste Funny to You?

**Summary for the Chapter:**

> Day 22: Drugged  
> Whumpee(s): Sam and Dean  
> No specific time period. Jack's around, but no specific events are referenced at all.

“Are you sure this bar is safe?” Castiel whispered to Dean as the four of them started to head inside from the parking lot. Sam and Jack were several steps behind, Sam answering one of Jack’s questions.

“Cas, chill. I’ve been going to these kinds of places since I was maybe ten years old. Besides, we’re all here, and this is just a pit stop. No monsters, no nothin’. Just a guys’ night out.” 

Cas grunted. Dean rolled his eyes.

“Seriously, relax. They’ll ID him, and that’s all.” At least Dean understood that Jack was the source of Castiel's worry. 

“This isn’t a place for a child,” Castiel started, but then they were at the door, Dean pulling it open. He wiped his hand on his jacket with a sound of disgust as they walked inside. 

Castiel didn’t understand humanity’s love for bars. The surfaces were often sticky, and the smell of alcohol and sweat permeated the air. He was sure there were nice establishments, somewhere, but the ones Winchesters tended to frequent were run-down roadsides filled with all kinds of people they knew nothing about. And humans could be monsters, too. Castiel wouldn’t worry if it was just himself and Sam and Dean, but with Jack… well. He found himself worrying about the little things much more often since Jack had been in the family. 

Jack's fake ID passed inspection just fine, and he Sam sat down with Castiel in a corner booth, while Dean went to the bar to get them drinks. 

“I don’t think I’ve ever been to a bar before,” Jack said, sounding excited. Sam gave him a small smile from across the table. 

“Well, first time for everything, right?” Jack beamed at Sam’s reply, looking all around the room in curiosity. Sam and Cas were looking around as well, but for a very different purpose. Threat assessment. Their eyes met, briefly, and Cas was relieved to find he wasn’t the only one worried. 

Dean came back with the drinks, plunking them down on the table. 

“Some good stuff for us, a beer for the kid.”

Jack looked confused, like he wanted to say something. Dean interrupted before he could. “You're still a lightweight, kid. Sorry.”

Jack wrapped his hands around the bottle and took a sip despite the furrow that remained in his brow. 

Sam and Dean started at their drinks, but Cas just stared at his. It wasn’t like he got thirsty- he just ordered drinks for appearances. So he didn’t take a sip for a while. 

The four of them laughed, having a genuinely good time. It was nice- with their lives they didn’t often get to have these moments of unburdened camaraderie. It was good to see his family happy. 

Sam and Dean were still laughing at some story they’d been telling, much more relaxed than they’d been in ages, when Cas noticed Jack frowning at his drink. Cas nudged him with his shoulder. 

“You alright?” he asked, keeping his voice soft. 

“I think so,” Jack replied. “I don’t like the way this tastes. It’s not like the ones I’ve had before.”

Castiel frowned. In his experience, beers all tasted the same. But then again, how different could molecules really taste? Still something about it rubbed him the wrong way. He looked back to Sam and Dean, who were still leaning over the table, gasping for breath through their laughter. 

“Are you dizzy, Sammy? I’m kind of dizzy. We got the real good stuff, huh?”

Sam kept laughing. “Uh huh. Yeah. _Really_ good.” He dragged out the last words, sending himself and Dean dissolving into giggles again. 

“Cas?” asked Jack in a small voice. “What’s happening?”

Anger thrummed in Castiel. If his instincts were right- he picked up his glass and took a drink. And there, laced in among the molecules and glaringly obvious to something like him- was a drug. 

Kicking himself for not finding it sooner, Castiel stood. “We’re going,” he said, and to his surprise Sam and Dean immediately acquiesced, leaning on each other to stand up and swaying on their feet. Jack shuffled behind him, nervous. 

“We’re going out to the car,” Castiel told Jack, who nodded. Castiel grabbed Sam’s arm, since he was the closest, and started leading him to the door. Jack did the same with Dean. Glancing around, Castiel saw the bartender’s eyes trailing them, and suspected he was the culprit. 

It was quite the ordeal getting Sam and Dean out to the Impala, since they would both start giggling again at random intervals, sending their bulk swaying in all sorts of directions. After Cas and Jack had managed to get them both in the backseat, Jack looked at him worriedly over the hood of the car. 

“Are they drugged? I’ve read articles about drugs. They’re very dangerous.”

“They are,” Cas said. “This one doesn’t seem to be, fortunately, other than the obvious side effect of incapacitation. Still...” He leant down, pressing his fingers to each Winchester’s forehead in turn. He could heal some of the damage, but not all of it. They would have to sleep the rest of it off. 

“I can try,” Jack said, and Cas nodded. Jack could likely heal them better than Cas could. 

“Get in the car and lock the doors. You can work on healing them while I’m inside.” 

“You’re going back inside? Why?” 

“I won’t be long. Just don’t unlock the doors for anyone except me. Okay?”

Jack nodded. “Okay.” 

Castiel waited until he heard the click of the lock once Jack was safely inside, and then he stalked back into the bar and straight over to the bartender, who regarded him with an arched eyebrow. 

“Y’all didn’t pay,” he drawled. 

Castiel dug out two twenties from his coat pocket and slapped them on the counter. “Happy? Good. Because you drugged my family, and I am _not_ happy with you.” 

The bartender laughed, snaking the cash along the counter and tucking it into his pocket. “Listen, man. People get roofied here all the time. I can’t control it.”

“I think you can. And I suggest you stop the practice immediately, or I will stop _you_.”

“Oh yeah?” the bartender stopped wiping the counter, turning to fully face Castiel. “And what are you gonna do about, it huh? You’re, what? A suburban dad with a shitty day job? Please.”

If a challenge was what he wanted, Castiel was not above a little intimidation. He flashed his eyes blue, letting his grace flare into the air in front of him, making the man’s eyes widen as he felt the static on his skin. Just enough awareness to understand he was among something other. He dropped the rag, stepping back, hands raised in surrender. 

“Okay, I’ll stop. Please don’t kill me!”

“See that you don’t start again, or I _will_ be back,” Castiel growled. 

“Okay, I promise. I promise!”

“I’m glad we’re in agreement,” Castiel said, turning and storming out of the bar. 

Jack unlocked the car for him, and Castiel was greeted with soft sounds of pain. Sam and Dean were both rubbing at their heads, undoubtedly nursing severe headaches. 

“I could mostly heal them,” Jack said, lookin apologetic. 

“That’s good, Jack,” Castiel assured, settling into the driver’s seat. He turned around to face Sam and Dean. “Are you alright?”

“Oh, yeah, we’re peachy,” Dean snarked. Sam answered with a groan from where his head was pressed into the window. 

“Well, maybe you’ll listen to me the next time I say I don’t trust a bar, Dean.” 

Cas turned the key in the ignition, backing out of the parking lot and on to the road. He’d drive them to the next town, and then they could find a place to sleep. Hopefully one without anyone in it who wanted to drug them.

“Point taken, Cas,” Sam said, voice pinched. 

“Yeah, yeah,” Dean said. “I’ll listen next time.”

Castiel allowed himself a small smile, repeating a phrase he’d said just minutes earlier, but in a gravely different context. 

“Well then. I’m glad we’re in agreement.”

**Notes for the Chapter:**

> Wouldn't it be great if Cas actually got to drive Baby in the show? Anyway, stan protective Cas for good health. And be careful out there- watch your drinks and research some of the common roofie-type drugs so you can know the symptoms and the tastes/smells, for the ones that have them. 
> 
> Reviews are always appreciated!


	23. What's a Wumpee Gotta Do To Get Some Sleep Around Here?

**Summary for the Chapter:**

> Day 23: Sleep Deprivation  
> Whumpee: Sam  
> Again, this one doesn't have a specific time it's set, other than Jack being around. Enjoy!

After the hunt, Sam was exhausted. It was about four in the morning, and he and Dean staggered into the motel room, barely making it through showers before they collapsed into their beds. Dean was out immediately, but Sam just sort of laid there. He kept his eyes closed, tried a meditation he’d worked on with Jess a few times. No dice. He got up, stretched, laid back down. Apparently he just wasn’t going to sleep tonight, despite his complete exhaustion. Great. 

So he read for a while, hoping it would make his eyes dry and tired enough for him to just pass out. When that didn’t work, he crawled back into bed and laid there, hoping for sleep that never came. 

\---------

The next day came the drive back to the Bunker, endless gray expanses of road and the motion of the car. Normally, that could put him right to sleep. But today, Sam just lingered on the edge of it, eyes shut, breathing slow, but not actually falling over the edge. He couldn’t remember this ever happening before. He didn’t know what was wrong with him. 

\----------

It went on for days. Not that he’d never gone days without sleep before, but in those cases it was intention or necessity. Now, Sam _wanted_ to sleep, had wanted to sleep for almost a week, and his body couldn’t seem to cooperate. 

With anything, actually, since the sleep deprivation was making him sluggish. He nearly broke a plate trying to wash it, and the stairs were becoming harder and harder to traverse safely. He had to half-ass an excuse to get out of doing the grocery run, since he didn’t trust himself to drive. 

Meds didn’t do anything either, just made him feel even more tired than before. 

On the fifth night, Sam laid in bed taking slow, even breaths. His muscles were relaxed, he could feel how slow his heartbeat was. But he wasn’t falling asleep. He scrubbed at his face with his hands, trying to prevent his breath from hitching. He threw off the blankets and stood up, wobbling over to the door on shaking legs. He stumbled through the hallway, going somewhere, where was he- library. Yes. Library. Books. Thoughts. Research. Fix. 

“Sam?” 

Sam looked up through blurry, bleary eyes to see Jack and Cas sitting at one of the tables, some board game forgotten between them as they looked at him in concern. Oh. Right. They didn’t sleep. Apparently, neither did Sam. He started laughing, too damn tired to care about how insane he must look. 

“Sam, are you alright?” That was Cas. Sam stopped laughing and tried to form a sentence. 

“Somethin’... sleep, Cas. Can’t sleep. Wrong.”

Cas stood up and walked over, looking at him critically, and placing a steadying hand on Sam’s shoulder when he swayed. Jack hovered behind him. 

“You think there’s something wrong because you can’t sleep?” 

Sam tried to follow the words, but it felt like the sound was just in one ear and out the other, pausing to take a brief swim in the mess of grey matter in between them in spite of it's obvious need for REM.

Sam nodded, or he thought he did. Cas frowned, pressing two fingers to Sam’s forehead. 

And then his knees were giving out, the world falling into a sweet, sweet darkness. 

\---------

Sam woke up, well-rested for the first time in what felt like ages. He was in his bed, and he had absolutely no idea how he’d gotten there. He stood, walking to the kitchen to get something to drink. 

Cas was in there making coffee, of all things. 

“You’re awake,” he said, upon seeing Sam come in. Why did he sound surprised?

“Uh, yeah. Why? What happened?” 

“You don’t remember?”

Sam shook his head, his heart rate picking up. When he had memory gaps…. Pushing that right back into its lockbox, Sam forced himself to speak. “No. What happened?”

“The last hunt you and Dean went on, the witch? They cursed you. You couldn’t fall asleep for almost six days. It’s no wonder you don’t remember it, you were delirious by the end.”

Well, that certainly hadn’t been what Sam was expecting. “Um… how did you fix that?”

“I was able to put you to sleep with my powers, and then Jack and I removed the curse. You slept for a day and a half.”

“Oh. Well, uh, thanks. For, uh- you know.”

Sam smiled at him, and Cas smiled back. “Of course, Sam,” he said, and he turned back to the coffee maker. 

Sam avoided the coffee, opting for water. After breakfast, he could really go for a nap.

**Notes for the Chapter:**

> I hope this was good, because let me tell y'all that writing about sleep deprivation while sleep deprived in the wee hours with the lights dimmed is very difficult, because my eyes keep wanting to shut. 
> 
> Comments are always, always appreciated! They really make my day every time you guys :)


	24. You're Not Making Any Sense

**Summary for the Chapter:**

> Day 24: Sensory Deprivation  
> Whumpee: Jack  
> Set sometime early season 14-ish. Jack has no powers but does have a soul. And it doesn't fit exactly with the human Jack timeframe because I totally forgot Rowena and Jack hadn't bonded until 14x07. So, whoops? Perfect world where we got more Rowena&Jack time, I suppose. I love their dynamic.

One minute Jack was standing in a dusty warehouse, watching as Castiel moved in on the witch they’d been hunting, and the next he was on his back, with a buzzing sound in his ears that slowly faded to silence. The last thing he remembered seeing was the witch flick her wrist at him, as Castiel went in for the kill. 

Jack opened his eyes, fear rising when he still couldn’t see, he binked, hard, but nothing changed. Could you go blind from hitting your head? He called out to Castiel, but no sound came out of his mouth. No, that wasn’t right, he felt the vibrations in his throat and chest, but he couldn’t hear himself. 

“Cas!” Jack yelled, or thought he did. Panic flared. He couldn’t see, he couldn’t hear- “Cas!”

A hand descended on his shoulder, and Jack nearly cried out, shaking and crying with the force of his fear. He felt a surge of grace wash through him, healing cuts he hadn’t known he had, and it was gentle and soothing. _Castiel._

Jack reached out until he had a handful of familiar trench coat and threw himself into Castiel’s arms. He could feel Castiel’s hands gently rubbing at his back, feel the vibrations of his voice, but he still couldn’t hear it. 

He tried to take a deep breath. “I can’t hear. I can’t see. Cas, I can’t-” 

One of Castiel’s hands found Jack’s and squeezed. Jack stopped trying to talk. He was probably way too loud anyway. Or maybe he was too quiet. He didn’t know, he didn’t- 

Castiel squeezed Jack’s hand again, the other one warm on the back of Jack’s neck. The meaning was clear- _it’s going to be okay._ Jack nodded, feeling tears falling down his cheeks. He didn’t like this. He couldn’t stop the steady thrum of panic in his chest, the pit in his stomach. He felt sick. 

Suddenly Jack was being lifted, an arm under his knees and an arm under his torso. The rush of vertigo was too much, and he felt himself yelp, flailing his arms. One of his wrists connected with Castiel’s face, and Jack tried to say “I’m sorry.” He didn’t know if it worked. 

It was worse without his feet on the ground, but he trusted Castiel. It was dizzying when he began to walk, though, so Jack wrapped his arms around Castiel’s neck and buried his face in his shoulder, trying to stop crying. Cas just tightened his hold.

It was only a minute or two before Jack felt the heat from the sun. They’d exited the warehouse, then, and would be at the car soon. 

Castiel stopped, and Jack could feel the heat coming from the metal of the truck they’d driven here. He was gently lowered into the seat, where the temperature was a few degrees warmer. He tried to keep his breathing steady. 

Jack felt Castiel moving to pull away, and grabbed his wrist on instinct. He didn’t want to be alone like this. He hated feeling helpless and scared. 

A hand smoothed his hair, lips pressed to his forehead, and then Castiel was gone and the truck door was shut. Jack wrapped his arms around himself, trembling. He didn’t think Castiel had ever done that before- kissed his forehead. It was nice. It made him feel safe. 

He still jumped when he felt the whoosh of the driver’s side door opening, but soon he felt Castiel sitting beside him. The car started up, the vibrations in the seat notifying him, and then Castiel reached over to take his hand again. 

Jack held on for dear life the whole way home. 

\--------

The truck stopped, and Jack felt a little bit less like he was floating. During the drive he'd felt like a ghost, but without sight or sound. He hadn’t liked the vibrations and feelings of the car, and he couldn’t see when they were going to turn, so it always caught him off guard. He was gripping Castiel’s hand so hard he was surprised he hadn’t broken the bones, but it was the only thing that reminded him he wasn’t alone. And that he was safe. 

Even if it didn’t feel that way. 

Castiel had to let go to get out of the car, and Jack tried not to cry again. His door opened, Castiel’s hands reaching in to pick him up again. 

“No!” 

Jack immediately felt bad for shouting. Castiel was only trying to help him, and now he sounded ungrateful. 

“I- want to walk.” He hoped his words were understood. 

Castiel took his hands, guiding Jack’s body to the side. He jumped out of the side of the truck, staggering forward into Castiel’s waiting arms. The drop down had felt more severe than usual. Cas began to guide Jack forward, one hand on his back, the other holding his hand. It was slow, but somehow less scary than being carried. The stairs were difficult, and slow, and Jack could feel Castiel’s grip tightening every step they went down. 

Eventually they reached the bottom, and Jack was led down a hallway and into his room. Castiel sat down with him on the edge of his bed. At least he assumed it was his room. 

Castiel shifted, still holding Jack’s hand loosely. His other hand started rubbing circles on Jack’s back. He hadn’t realized how tense he was until he felt himself start to relax in his exhaustion. 

The bed sank on Jack’s other side, and he jumped. Cas squeezed his hand. 

Jack’s other hand was gently tilted so that his palm was facing up, and he felt letters gently traced into his skin. S-A-M. 

“Sam?” He said.

Sam squeezed his hand, and pulled Jack into a side-hug, his chin on Jack’s head for a moment. From that position Jack could feel the vibrations that indicated Sam was talking. After Sam pulled back, a third hand descended onto Jack’s shoulder. Sam tilted his palm over and traced a single letter. D. 

Jack smiled, feeling more relaxed with his whole family here. They’d find a way to fix him. They always did. 

F-O-O-D? Sam traced the question into his hand. 

Jack nodded. He didn’t want the frustration of not hearing what he said. What if they couldn’t fix it? What if he was like this forever? 

As his breath picked up, Castiel started rubbing circles into his back again. His breathing eased just a bit. 

Sam squeezed his hand before letting go, keeping a hand settled on his shoulder. A glass of water was eased into the hand Sam had let go, cold and wet. Jack carefully lifted it to his mouth and took a few sips. 

Castiel squeezed his hand. 

Jack worked his way through a sandwich and another glass of water, and then his eyes couldn’t stay open anymore. Just because he couldn’t see didn’t mean his eyes weren’t still dry and tired. Once his head slipped down to Castiel’s shoulder for the fourth time, Sam once again flipped his hand, meticulously tracing out the longest word yet. 

G-O-O-D-N-I-G-H-T

Jack relayed the sentiment best as he could, and then Sam and Dean were off, Sam with a squeeze of his hand and Dean with a ruffle of his hair. 

He let out a shaky exhale, once again fighting back tears. Castiel was shifting, trying to ease Jack down to the bed, but Jack didn’t want him to leave. He laid down so that his head was on Castiel’s chest, and positioned himself so that his father could keep an arm around him. 

Castiel was back to rubbing patterns on his back, soothing him to sleep. Jack gripped the trench coat in his fist, fighting to keep his breathing even. A few tears slipped out against his will, soaking into Castiel’s shirt. Castiel pressed a kiss to the top of Jack’s head, and held him as he silently cried himself to sleep. 

————-

Jack woke up nestled against Castiel, and he couldn’t remember why until he opened his eyes. That was when the panic came back in full force. Castiel helped him sit up, a steadying hand on his back. He was handed another glass of water, and he drank some gratefully. 

Another set of hands, presumably Sam, turned over the same hand as yesterday. The letters on his palm were different, though. R-O-W-E— Jack cut him off. 

“Rowena? Rowena’s here?” 

Sam squeezed his hand, and then passed it off to a cooler, softer and smaller hand, with long nails. Rowena retrieved his other hand, and Castiel’s constant presence also moved away. Panic flipped in Jack’s stomach again, but one of Rowena’s cool fingers turned his head, presumably so she was looking right at him. It was a long few minutes of Rowena tapping at his face, and then her hands pressed into his temples. Hard. 

Stars erupted in his eyes, and a loud blast sounded in his ears. 

He blinked, and his vision cleared. _His vision cleared._

Jack looked at Rowena, at the brilliant red of her hair and the bold lines of her makeup. 

“Can you hear me, dear?” She asked, and Jack was _thrilled_ to hear her voice. 

“I can,” he said, feeling tears forming again. 

“Right, good. Nasty curse that was, though I’ve been informed you handled it very well.” Rowena smiled, helping him to his feet. “Let’s go stop the fretting of your fathers before they worry themselves to the grave.” 

“Thank you, Rowena,” Jack said earnestly. 

“Och, it’s nothing, lad. Your Auntie Rowena is always just a call away.” 

They rounded the corner to the kitchen, and Jack smiled at the sight of his fathers sitting around the table. The browns of the bunker walls and Castiel’s trench coat, the blue of his eyes and Sam and Dean’s jeans, the greens of their eyes- all the colors were so _beautiful._

They rushed over to him, exclamations and questions assaulting his ears while their worried expressions assaulted his eyes. 

Jack just smiled, thrilled to be able to see and hear them again.

**Notes for the Chapter:**

> This was the first one of the prompts I wrote, and I have been SO excited to post it. I hope y'all liked it!
> 
> Thanks for reading! Comments always make my day :)


	25. I Think I'll Just Collapse Right Here, Thanks

**Summary for the Chapter:**

> Day 25: Disorientation  
> Whumpee: Castiel  
> Again, no idea when this is set beyond a vague "late seasons."   
> Also, it's another loose interpretation of the prompt. I did actually look up the symptoms of disorientation, and for whatever reason all my brain latched on to was not recognizing your loved ones. This was the result. I hope y'all enjoy it.

The world was spinning, and it wouldn’t stop. Castiel was in pain. That was all he knew- that his wings were twisted in ways they shouldn’t be, his grace was far too weak and he could feel pain in every inch of his vessel’s skin. Feel the blood dripping off that skin, warm and foreign, feel the organs convulsing with some kind of drug. He could feel thick needles through the skull, piercing the brain. The agony was excruciating. 

Thought, cognition- it was out of reach. The pain was all he was reduced to, trapped in, and all he could do was scream and wait for the Host to retrieve him. But that wasn’t right- there was something, something he was forgetting- 

The hazy tendril of memory was ripped away as a blade jammed into his vessel’s leg, piercing flesh and muscle and tendon all the way through to the chair he was strapped to. 

The pain took over again, and Castiel kept screaming.

\----------

The impala buzzed down the highway, ten miles over the speed limit and counting. Dean had the gas pedal pushed to the floor, and Sam had his phone’s GPS out. Jack sat in the backseat, wishing there was something he could do to help. 

“Six more minutes,” Sam said, anxiously watching the icon that represented the impala moving closer to the blinking dot of Cas’s phone. 

“Not good enough,” Dean grumbled, speeding up further. 

Sam’s jaw worked, and he glanced out the window at the trees as they rushed by. 

Cas had been captured. They didn’t know by whom, but they’d had him for days. Sam had only just managed to locate the tracker in Cas's phone, and they had all piled into the impala the minute he had. The only issue was that they were flying in blind, with no idea what they were up against. And they didn’t know how bad Castiel was hurt. 

In a blink, Jack doubled over with a yelp, loud enough to make Dean jerk the wheel. A sound was splitting his brain open, a raw scream of pain coming over angel radio. It faded out with a ringing left in his ears, and Jack looked up once his head cleared to see Sam looking back at him in open fear. Jack blinked, realizing his cheeks were wet. 

“Jack, what happened? Are you okay?” Sam’s voice was frantic, and Jack knew Dean’s eyes were on him in the rearview mirror. He swallowed, hard, but his voice still came out strangled and weak.

“That was Cas. On angel radio.” He glanced between Sam and Dean, who’s faces both dropped. “He was- he was _screaming_.”

Jack hadn’t known it was possible for the impala to go any faster.

\----------

The three of them clambered out of the car once they made it to the warehouse Cas’s phone signal came from, stocking up with guns loaded with silver bullets and an angel blade each. Jack could still hear the short bursts of agonized screaming, and he knew they were in the right place. 

And so the fight began.

\----------

Pain was all Castiel knew, and then there were hands. Human hands on his shoulders, human voices chanting a shortened version of his name. He didn’t understand. Why had the Host not come for him? 

The humans pulled the spikes out of his vessel’s brain though, murmuring assurances as they went. Castiel felt as if he were floating, staring right through them. Like when he and Balthazar had snuck beyond Heaven’s gates as fledglings and watched the humans from above the clouds. Floating beyond the reach of humanity. 

The two humans stepped aside, and Castiel felt another presence. A nephilim. Castiel recoiled, falling from the chair he’d been chained to until he was pressed against the wall, leaving a wet, sticky trail of his vessel’s blood on the floor. What was such an abomination doing here? 

“Castiel?” The nephilim knew his name. “Cas, it’s okay. I’m just going to heal you.”

Castiel took a long look at the nephilim’s grace, and _recognized_ it. 

“Lucifer is your sire,” he snarled. The nephilim reacted as if Castiel had struck him, staggering back a step.

“I-”

“Heaven dictates that all nephilim are to be killed before birth, or immediately following. There should not be one existing in this world.”

The child took another stumbling step back, where the taller human caught him, staring at Castiel like he’d somehow betrayed him. Ridiculous. An angel of the Lord did not associate with humans, he’d been taught that from the beginning. And they certainly did not form close enough bonds for any sort of betrayal to occur. 

Castiel looked at the inexplicably living nephilim boy again, and lunged. 

\----------

Cas lunged at them, still dropping blood from a multitude of wounds and sporting several broken fingers. His face was blank, and he seemed to be looking right through them. 

Dean jumped forward to try and calm Cas down, while Sam swept Jack to the side. Jack was shaking, he realized. Because Cas might not be _seeing_ any of them right now, not really, but he’d looked directly at Jack and seen Lucifer. And that _hurt_. 

“Jack,” Sam said, pulling back to look at him but leaving his hands on Jack's shoulders. “It’s not him. He doesn’t recognize any of us right now, he’s- they must have done something to him. Those spikes, they access basic programming for angels. They must have wiped out a few memories. But it’s not our Cas. You know he’d never say that stuff to you.”

Jack swallowed, watching as Cas and Dean grappled. “If he’s lost memories, will he ever get them back?”

“He has to,” Sam replied. 

“Dammit, Cas! It’s me, it’s Dean! Winchester!”

The name made Castiel pause for half a second, barely at all, but it was enough. Enough for them to know what to do. 

“Cas, it’s Sam. We’re here, we’re right here. You can fight this!” 

“Hear that, buddy?” Dean continued, out of breath from the fight and still light on his feet, wary across from Cas. “The Winchesters. Your friends. Your family.”

Cas had stumbled so he was leaning against the wall, a hand pressed to his temple. His face was contorted in pain. But he wasn’t fighting them, so maybe it was working. 

“Cas,” Jack stepped forward, pulling away from Sam. “It’s me. It’s Jack. I’m- I’m your son.” It felt strange to say. He’d never called himself anyone’s son before, only referred to others as his parents. 

That didn’t make it any less true.

Cas gasped and collapsed to the ground, still bleeding from everywhere. 

“Cas?” Dean stepped forward, tentatively. Jack made to follow, but Sam stopped him with a hand on his shoulder. 

Cas looked up, eyes exhausted and pained but finally focused, the disorientation over. 

“Dean?” he said, and Jack felt himself sag in relief. Cas was back. _His father was back._

Jack and Sam hurried over, Jack leaning down to heal Cas’s injuries. 

Cas looked at him, so much sadness in his eyes. “Jack, I’m so sorry. I would never-” 

“It’s okay,” Jack was quick to reassure. “I know. You weren’t…” Jack glanced at Sam, who nodded at him in encouragement. “You weren’t you.”

Castiel’s shoulders relaxed in his relief, and he reached out a hand to grip Jack’s. 

“I love you,” he said. He glanced up at Sam and Dean, standing over Jack and Cas on the floor. “All of you. And I’m so sorry-”

“Cas,” Sam cut him off, shaking his head. “Don’t. There’s no need.”

“Yeah, man,” Dean added. “We’re just happy to have you back.”

And Jack agreed. Though he knew he’d always have Sam, and Dean- it wasn’t quite right without Castiel. There’d been something off, a piece missing without Castiel. And now that he was back, and was alright, it was like the sun coming out after a storm.

It felt like the world had finally stopped spinning and gone back into focus.

**Notes for the Chapter:**

> Overly sappy? Me? Actually, that was probably a pretty predictable thing for me to do, ngl. 
> 
> Thanks for reading, as always! Y'all are awesome.


	26. If You Thought the Head Trauma Was Bad...

**Summary for the Chapter:**

> Day 26: Blindness  
> Whumpee: Sam  
> Set sometime in season 2

Getting hit on the head was part of the job, and it had been happening to Sam for years. He was only 23 and had experienced almost as many concussions. It’s a wonder he hasn’t had any brain damage, despite all of Dean’s jokes that his hair was good enough padding. 

This salt and burn the ghost sent Sam flying, head colliding with a solid gravestone. All business as usual. 

The distinctive roar of the flames in the grave erupted, and Sam heard Dean whooping at another hunt well done. Sam, though, was doubled over, eyes squeezed shut as he waited for the waves of pain to subside. 

He opened his eyes, and blinked again, and again, and yet again, because he couldn’t see. He couldn’t see. He was blind.

“Hey, Sammy, you alright?” Dean’s voice rang out loud and clear, but Sam was still frantically blinking from his place on the ground, swirls of panic in his stomach and his head fuzzy. 

“Sam?”

Sam opened his mouth, but couldn’t make any sound come out. His heart was beating triple-time, his mind chanting a chorus of “no, no, no, no, no.” 

Dean’s hand descended on his back, and Sam nearly jumped a foot off the ground. 

“Hey, hey, easy. You okay?”

“Dean,” Sam choked out, his throat tight. The hyperventilating wasn’t making it any easier to speak, either. 

“Yeah, it’s me, what happened?”

“I can’t see,” Sam whispered, a hand taking Dean’s jacket in a death grip. “Dean, I can’t see.” 

Dean was silent, but Sam could hear his breathing. 

It got to be too much. “Aren’t you gonna say something?” Sam snapped. 

“Okay,” Dean said, voice poorly concealing panic. “Okay. Uh, I’m gonna get you to a hospital, okay? They’ll figure it out. It’s probably temporary.” 

Sam clenched his jaw. He knew enough about head trauma to know that it might very well be permanent. 

“Can you walk?” Dean asked.

“It’s my eyes that are screwed up, Dean, not my legs.” 

“Right. Up we go.” 

Sam let Dean help him to his feet, but then he yanked his arm away. “I can walk fine. I don’t need help.” 

Sam took four steps forward on his own and then fell flat on his face, having tripped over another grave marker.

Dean dragged him back up, and didn’t let go of his arm again. “Can walk fine, my ass,” he said, leading Sam to the car.

Sam desperately tried not to panic as the car whirred to life, speeding out of the parking lot.

\---------

Fortunately this one hadn’t been a blood and guts kind of hunt, otherwise they’d have a whole lot of difficulty explaining what they’d been doing. As it were, Dean figured they could spin a story about Sam having fallen in a fit of lanky-limbed clumsiness. Which should be enough explanation for the dirt on their clothes, too. 

So he led Sam into the local hospital in the wee hours of the morning, thankful it was even open. As soon as he felt a chair, Sam sat down in it heavily, crossing his arms. He was grumpy, but Dean knew him well enough to know it was masking fear. 

“I’ll be right back, okay? Just gotta get the paperwork done.” 

Sam nodded, eyes blankly ahead. It was disconcerting. “Yeah.”

Okay, one word responses were concerning, but all Dean would do was squeeze his shoulder and walk away. He went to the front desk, where the tired-looking lady was looking at him over glasses.

“What’s your emergency?” she asked. She sounded vaguely like the receptionist from Ghostbusters.

“Well, my brother there-” Dean gestured in Sam’s direction. “Sorta fell and hit his head on a stone wall. He’s clumsy, happens all the time. But this time, he uh- he can’t see anything now.” 

Saying those words felt like taking a cheese grater to his tongue. It stung, and he just wanted them to be gone. 

The desk lady sprang into action, though, calling for a doctor. Dean gave her some half-assed fake insurance info, and walked over to sit with Sam. 

“Should be just a few minutes,” he said, bumping Sam’s shoulder with his own. 

Sam just kept staring straight ahead, barely grunting in acknowledgement. 

Dean wished he knew what Sam was thinking.

\-----------

Sam felt like he was floating, not anchored down to anything. It was really quiet in the waiting room, which made sense since it was three in the morning, and he could hear Dean talking to the front desk lady, but it sounded like it was coming through a pipe. It was distorted and miles away. 

Dean plopped back down next to him at some point, and he was talking then, too, but Sam just wanted to tune everything out. 

He was still out of it when Dean grabbed him by the arm and started leading him after the Doctor. 

“Sam!” Sam blinked, before remembering that wouldn’t do anything. 

“Sam, you with us?” That was Dean’s voice. Sam nodded, realizing he was sitting on an exam table now. 

“Good.” Sam swiveled his head towards the new voice, instantly wary. Dean was standing close enough that Sam could feel his body heat, though, and he didn’t flinch. The voice belonged to the doctor, then. 

“I’m Dr. Cleveland. I just have a few questions and tests, and then we’ll get you a diagnosis, okay?”

\---------

Temporary blindness. Thank whatever was out there it wasn’t permanent, but this was going to be a bitch to deal with in the meantime. After maneuvering a bitchy but relieved Sam to the passenger seat, Dean scrambled around to the driver’s side. He wanted to sleep for a week after that hunt, and it wasn’t like he could let Sam drive right now. Might was well hurry to their destination. 

“Where are we going?” Sam asked from behind sunglasses as they pulled out of the parking lot. They really did have to go, and fast, because the fake insurance wouldn’t hold up under scrutiny for long. 

“Bobby’s. Safe place for you to stay till your brain fixes itself.”

“What are you gonna do?” Sam asked. 

Dean fought to keep his jaw from dropping, and then remembered it was pointless because Sam couldn’t even see him. 

“What do you think I’m gonna do?” 

Sam exhaled in relief, which Dean elected not to unpack. “I don’t know. Keep hunting?”

“Best to have a partner for that, you know,” Dean said, pulling onto the highway. 

Sam’s lips quirked up in Dean’s peripheral vision, just barely. Just enough. “You do need someone to make sure you don’t make a fool of yourself.”

Dean smiled, Sam laughed, and they sped down the highway. 

\-----------

By day four of just sitting on Bobby’s couch, Sam was losing his mind. He couldn’t do anything beyond listen to the radio, which had Dean making snide comments by the second day. Bobby had managed to scrounge up a few audio books for him, which Sam promptly devoured. 

One of them would bring him food whenever Dean and Bobby actually made a meal in the kitchen, but that job was delegated to just Bobby after Dean had decided to prank Sam for the third time by putting the meat on the outside of the sandwich, which had Sam dropping the plate and breaking it in surprise. 

Bobby laying into Dean had almost been worth the heart attack, even if Sam couldn’t see Dean’s face to properly enjoy his younger sibling moment of triumph. 

By day five, Sam was seeing outlines of shapes and colors again. He was so relieved he could cry. 

By day seven, everything was back to normal. Bobby insisted they stay another day to make sure everything was back for good, and that was fine by Sam. 

He did need to think of a way to prank Dean back, after all.

**Notes for the Chapter:**

> I hope y'all don't mind that these end up being much more light-hearted than straight up whump, ahaha.
> 
> Reviews are much appreciated!


	27. Ok, Who Had Natural Disasters on Their 2020 Bingo Card?

**Summary for the Chapter:**

> Day 27: Power Outage  
> Whumpee: This literally isn't whump. It's pure fluff. I'm very excited about it though, so I hope y'all like it!  
> Once again, just set in a vague *later seasons* kind of zone.

“Aw, come on!” Dean’s shout wasn’t panicked, exactly, more… annoyed. But it accompanied all the lights going out in the Bunker, and so Jack leapt to his feet and started running out of his room. He ran straight into Sam.

“Whoa, Jack, are you okay?”

“What’s wrong? Why are all the lights off?”

Sam’s lips quirked up, slightly, and he didn’t look worried at all. That’s when Jack started to relax. 

“It’s just a power outage. Dean said he was gonna do some tinkering on the generator, so he probably hit a wire he wasn’t supposed to. I’m sure it’s all fine.”

“Oh. Okay.” Jack hadn’t really thought about the power ever failing. He’d never had that happen before.

He and Sam walked into the library, where Dean was coming in the opposite door. 

“Damn generator crapped out on me. Power’s gonna be off for about five hours before it boots up again,” Dean said, wiping his hands on a rag.

“Five-” Sam took a deep breath. “Dean, I have research I need to do, and my laptop’s dead.”

“Well, sorry, Sammy,” Dean said sarcastically. “But I thought you’d want to have the glitches in the power grid fixed up.” 

“There _aren’t_ any glitches in the power grid, Dean. The power has been fine the entire time we’ve lived here.” Sam was pinching the bridge of his nose, looking very tired. 

“Well,” Dean grinned. “There’s glitches now.” 

Sam rolled his eyes. “Dean-”

“What’s happening?” Castiel came into the library then, looking around curiously. “Did you turn all the lights off?” 

“Dean decided it would be a good idea to screw with the power generator,” Sam said dryly. 

“Hey, I wasn’t screwing with it. I was _tinkering_. Right, Jack? Tinkering?” 

Dean looked at him in a way that suggested he was supposed to go along with it. Jack didn’t get it. 

“Um. Yes. You were tinkering,” Jack said, trying to sound convincing. 

Sam was still shaking his head, but there was a tiny smile on his face. Cas just looked confused, and Dean grinned again. 

“See?” Dean said. “Kid gets it.”

“Okay, just- just stop. What are we going to do for the next five hours?”

They looked around in silence for a few moments, all of their faces bathed in shadow. And then Jack smiled. 

“I have an idea!”

\------------

They cleared a space on the map table and set up flashlights all around it, creating a circle of light. Sam made up a bowl of trail mix and Dean grabbed them several beers, claiming they’d all get warm without the power on anyway, so they might as well drink 'em cold.

Cas and Jack were tasked with deciding what challenges they would face today. They didn’t understand half of the titles on the colorful boxes, though, so they just picked up armfuls that they thought looked interesting. 

And then the games began.

\------------

Scrabble very quickly turned into a duel between Sam and Castiel while Dean and Jack finished their turns as quickly as possible to allow Sam and Cas space to continue their death match. 

“Hey, kid. I’ll bet you three candy bars that Cas has got this in the bag.” Dean whispered, leaning over to Jack.

Jack looked at his other two fathers, arguing about whether or not “ain’t” was a valid Scrabble word when they couldn’t simply google it, as everyone’s phone was dead or almost dead. Jack thought Sam had a fighting chance. 

“Deal,” he whispered back, shaking Dean’s hand under the table. 

He shouldn’t have underestimated the kind of vocabulary millions of years of life could build up. 

\-------------

Pictionary was… interesting.

Jack and Cas were teamed up against Sam and Dean. It became apparent very quickly that Sam could not draw very well, much to Dean’s frustration. Cas was surprisingly good at it, Dean was passable, and Jack wasn’t much better than Sam. Cas was good at interpreting his scribbles, though, and so Jack and Cas took the win.

\-------------

“What about this one?” Jack asked, holding up a simple black box with white lettering on it. 

“I’m not familiar with this game,” Cas said, taking it from Jack and setting it on the table. “Sam, Dean? Is this one acceptable?” 

Sam and Dean turned and looked at the box on the table. Dean started laughing, throwing his head back as his whole body shook. Sam’s eyes widened, almost comically, and he reached out and yanked the game away. 

“When did you buy this, Dean?” Sam growled, glaring at his brother. 

“Gift from Charlie, man,” Dean said, wiping his eyes. “I think it’s a great idea. Let’s go, right now.” 

“What’s wrong with it?” Jack asked. 

Sam glanced from Dean back over to him, looking lost for words. “Umm… it says you have to be 17 or older to play. Sorry, Jack.” 

Jack nodded, still confused. He’d have to figure out later what was so bad about Cards Against Humanity.

\-------------

Mousetrap was fun for a while, but Dean had clearly been practicing with the board. He won far too easily. 

\-------------

“Sam, if you buy Boardwalk too I swear to God I’m gonna…” Dean trailed off as Sam purchased the property, shifting his game pieces accordingly. 

“You’ll what, Dean?” Sam asked, smirking. “You’re just upset because you’re in jail. Again.”

“Kid’s already got all the railroads. All the good stuff is gone!”

As Sam and Dean bickered, Jack leaned over to Cas. “And what should I do next?” 

“Well, you’ve got to stop Sam from getting Park Place. So the next thing to do is....” 

Jack won Monopoly, with a grinning Sam in second place. Cas winked at Jack, who beamed at him. 

Neither Sam or Dean suspected a thing. 

\-------------

“Hey, Cas, you got any sevens?”

“No, Dean. You must go fishing.” 

\--------------

Jack was disappointed to find there was no actual candy involved in Candyland, but he did like the colors. Sam and Dean were neck and neck for the victory in this game, but Sam took it in the end, leaving Dean behind by a mere single space on the game board. He grumbled about it, but he was smiling.

\-------------

Clue proved to be no fun with a family of trained supernatural investigators. Dean did say they would have to watch the movie on their next movie night, though, so Jack had that to look forward to. 

\-------------

They played until the lights came back on, and a little beyond that. Eventually, Sam and Dean left to go to sleep, cleaning up beer bottles and the now-long-empty bowl of trail mix as they went. Cas and Jack packed away most of the board games, and Jack supposed he should go to sleep too, even though he didn’t really need it. 

“Jack,” Cas said. Jack turned to see him holding up one last board game, this one quite familiar. “Would you like to play one more?”

Jack grinned and sat down to play Connect 4 with Cas, deciding that in spite of today containing his first ever power outage, it had been one of the best days ever.

**Notes for the Chapter:**

> A game night episode would have been SO GOOD. They faked us out with the episode Game Night, which was... actually really depressing. ANYWAY, I guess I'll just live off of that one scene with Cas and Jack playing Connect 4. :)
> 
> Thanks for reading! I hope y'all enjoyed this sugary treat instead of your daily dose of pain, ahaha.


	28. Such Wow. Many Normal. Very Oops.

**Summary for the Chapter:**

> Day 28: Mugged  
> Whumpee: Dean   
> Set season 1, because I'm feeling nostalgic.

Sam looked up as Dean walked into the motel room, eyes widening at the look on Dean’s face. And the massive shiner he was sporting.

“Dean, what the hell happened?”

Dean mumbled something, shuffling to the fridge and grabbing a cold beer to press over the bruise on his eyes. 

“What was that?” Sam asked, still not sure if he should be worried. 

“I got mugged.” 

Sam had to actively work to keep his jaw from dropping. And not to laugh. He was sure this was a _very_ serious situation. 

“You, uh- you got what, exactly?”

Dean turned to glare at him, the effect dampened by the bottle he was holding up and the fact that he was _clearly_ wasted. 

“I got mugged, okay?”

Sam stifled another laugh, standing up to move a little bit closer. “Are you okay? Besides the eye, I mean.”

“No, Sam. I got mugged. They got my money,” Dean honest to god pouted like an eight-year-old, and Sam couldn’t help it anymore. He doubled over laughing, clutching his stomach and gasping for breath.

“It isn’t funny!” Dean sputtered, which just made Sam laugh harder. “Stop laughing, Sammy. I worked _hard_ for that cash.” 

“You hustled for it, didn’t you?” Sam managed, having come down from the peak of his laugh attack.

“Well, duh.” 

“Okay,” Sam said. “Looks like you took the act a little too far, and actually got wasted. And then you got jumped, dude. Oh, I hope you remember this. Because even if you don’t I am not gonna let you forget it.” 

“Screw you, Sam.” 

Sam just grinned. After all, more big-brother-blackmail material was _never_ a bad thing.

**Notes for the Chapter:**

> Short and sweet. I miss when the boys actually like... smiled. :(
> 
> Thanks for reading! We're in the home stretch of these now, and if you've been sticking with me this whole time I am sending you a virtual hug. You rock. (Or if you just jumped in! Thank you!)


	29. I Think I Need A Doctor

**Summary for the Chapter:**

> Day 29: Intubation  
> Whumpee: Jack  
> Set in that bit of season 14 where Jack and Cas were off doing father-son bonding on monster hunts, but we didn't actually get to see any of it :(

It all happened in flashes. Whatever Cas and Jack had been hunting had some technology they said they’d stolen from the British Men of Letters, and when it fired it locked down Cas’s powers. Jack barely remembered that, because a moment later he couldn’t breathe. 

Everything after that was a blur. He remembered pain, though. Lots of it. 

Now, he woke up and knew something was _wrong_. He started choking, trying to get his hands up to his throat, get rid of whatever was there that wasn’t supposed to be, but something was holding his hands in place. He tried to scream for help, but he couldn’t. Something was very wrong, but he couldn’t do anything about it. He was trapped. 

“Jack, Jack, it’s alright.” Cas?

Jack tried to turn his head, and then instantly regretted it when it pulled at his throat. 

“Stay still, Jack.” That was Cas again. If he was here, it had to be fine, right?

Jack tried to take a deep breath, but something was in the way of that, too. 

A different voice, crisp and clear, rang out. “Just let it breathe for you. Relax.”

Jack stopped panicking, and though it felt very odd, he allowed whatever was in his throat to pump air down his throat for him. He didn’t like it. 

He opened his eyes, looking up to see two strangers and Cas. He looked right at Castiel, hoping his eyes conveyed all of his questions. A hand found his and squeezed. 

“You’re alright, Jack. I’m here.”

“You’ll have to stay intubated for a few more hours, just so we can be sure there aren’t any complications. You’ve been sleeping for a day and a half, while we got your dad here back on his feet,” said one of the doctors, smiling at him. She seemed kind enough.

“Try to get some rest,” said the other doctor. “We’ll be back soon to take out the tube, alright?”

“Thank you,” Castiel said, for him, and the doctors left the room, shutting the door behind them.

Jack tried to stay calm, and failed miserably. Cas was there to squeeze his hand, though. 

“I’m so sorry, Jack. Whatever that device did to me, I still can’t use my powers. Otherwise I would have healed you.” 

Jack tried to squeeze Cas’s hand back, but it didn’t seem to work. He was very tired, now that he wasn’t scared. And with Cas here, he knew he was safe. He was always safe with Castiel. 

Jack closed his eyes, and he felt one of Cas’s hands smooth his hair back. 

“Sam and Dean are on their way.” Cas’s voice was soft and soothing. “And I’ll be right here.” 

Jack succumbed to the darkness. 

\----------

When he woke up again, he was breathing on his own. He coughed a little bit, since his throat now felt scratchy, but it was much better being able to swallow and shift around. He still couldn’t remember what happened, though. 

“Hey, Jack.” That was Sam, standing there with Dean and Cas. “Ready to go home?” 

And Jack nodded, still out of it, but happy to be going home with his family.

**Notes for the Chapter:**

> This one just did NOT want to get written, and I have no idea if it's any good. I've also never been intubated so I don't know if it's accurate in the slightest. 
> 
> Anyway. I hope y'all enjoyed it. Thanks for reading! Only two more left, and hopefully they won't feel like pulling teeth to write like this one did.


	30. Now Where Did That Come From?

**Summary for the Chapter:**

> Day 30: Ignoring an Injury  
> Whumpee: Cas  
> It's not set anywhere, really. I guess it kind of starts after Cas got his grace back from Metatron in season 10.

When Castiel got his grace back, or the tatters that were left of it, the pain caught him by surprise. But he’d soon get used to it. 

There were always battles to be fought and family to save, after all. He didn’t have time to waste on broken wings. 

\---------

He wondered idly, some days, if Sam and Dean realized his wings were still there. Always throbbing, aching in a dimension he kept close behind him, twisted and mangled beyond recognition. He used to think his wings were somewhat impressive- Dean had been sufficiently awed by them when he’d first seen their shadow, after all. Now, it was probably a good thing that the Winchesters’ understanding of the Fall amounted to “angels can’t fly anymore.”

If they knew, he didn’t know how he’d be able to stomach the shame. 

\---------

In interacting with other angels, it was a given not to discuss it. They were all in pain. But Castiel didn’t miss, _couldn’t_ miss the whispers, the angry fluttering of broken wing bones held close to the body that once upon a time would have signified some show of dominance, of threatening. Some days, Castiel could feel the hatred of his siblings, practically taste it as it assaulted every sense. All the angels left alive didn’t care for him anymore, if they ever had. And with the role he’d played in condemning them to lifelong pain, he couldn’t really blame them.

Even if it meant he had to pretend he wasn’t constantly burning under the sting of rejection, too. 

\---------

He didn’t know what Jack could see. Didn’t know if Jack saw his vessel with a thrum of tired grace humming under the skin, or if he could see the wave of light cramped inside, bloodied and beaten, tattered wings held close. 

Jack never asked why he couldn’t fly, which was for the best.

This pain was a burden that never needed to be shared.

**Notes for the Chapter:**

> I just really wanted to talk about Cas's wings again. It makes me sad to think about. 
> 
> Sorry this was so short! I've had tomorrow's planned for a while so hopefully it'll be nice and long to make up for the short chapters lately. 
> 
> Y'all are the best! Thank you for sticking with me! Just one more chapter to go ;)


	31. Today's Special: Torture

**Summary for the Chapter:**

> Day 31: Experiment  
> Whumpee: Everyone? But Dean and Jack specifically.  
> Set somewhere in season 14, Jack has powers and a soul :)  
> Last chapter! It's nice and long to make up for all the short ones lately. I hope you like it!

Sam woke up with a splitting headache and a million questions spinning in his mind. He opened his eyes, and was instantly on high alert when he didn’t recognize the room. He sat up, ignoring the rush of vertigo, and tried to stand, only to fall back down when his muscles didn’t hold him. His very bones were aching. 

He looked around again, realizing he was in a bedroom. One that looked lived in, but not as much as one would expect. Like Sam’s room in the Bunker. 

The door opened, and Sam got into as much of a defensive position as he could, but relaxed as soon as recognition registered. 

“Alex?” he said. 

She nearly dropped the glass of water she was holding in surprise. 

“Sam! You’re awake.” to his surprise, she set the water down and threw her arms around him. He hugged back as best he could, still dazed. 

“Alex, uh, what happened? Is Jody around?”

Alex pulled back, brushing her hair behind her ear. “She is. Um. There’s a lot you need to know. How are you feeling? Can you walk?” 

“I’ve been better.” Sam forced a smile. Alex could probably see right through it. “And I might need a hand, but I can get there.”

“Okay.” Alex helped him up, and he tried not to lean on her too much as she led him into Jody’s living room. 

Sam had hardly let go of Alex to lean on the wall before an armful of angel barreled into him. 

“ _Sam_ ,” Cas breathed, sounding like Sam had just come back from the dead. 

Sam awkwardly patted Cas on the back a few times before Cas let go, a hand still on Sam’s shoulder and a sad look in his eyes. 

What in hell was going on? 

“Hey, Sam,” came Jody’s voice, sounding thick with tears. She pulled him in for a hug, too, pressing her lips to his cheek. 

“Jody, Cas. Um. What’s going on?” 

They exchanged a look, and it wasn’t a good one. 

“Where’s Dean?” Sam asked, heart sinking as he realized there were people missing. “And Jack?” 

Cas winced, looking to the floor. 

“They’re missing, Sam,” Jody said softly. Sam felt his heart drop, and he stumbled, three sets of arms reaching out to catch him. Cas and Jody led him to the couch, Cas sitting down next to him and Jody staying standing. 

“Alex,” Jody said, tone gentle and firm. 

Alex nodded, fidgeting in the corner of the room. “I’ll go see if Patience has found anything new,” she said, exiting the way she and Sam had come in. 

“They’re missing?” Sam said. “Wha- when? How long?”

“A week,” Jody said softly, as Cas wrung his hands beside Sam. 

“What- what happened to me? I don’t remember anything.” 

“You and Dean and- and Jack,” said Cas, stumbling over their names, “Had finished a hunt near here. I was coming to meet you to take another in Iowa, but you were jumped. We don’t know by whom, but they had- they had cuffs that could hold Jack.” Cas’ voice was burning with anger, but Sam knew him well enough to hear it for what it was hiding, too- fear. “And they drugged you, and Dean. I got there just in time to get you away from them, and then you spent nearly three days in the hospital so they could drain the drug from your system. Then we moved you back here, and you’ve been in and out since then. This is the first time you’ve been fully awake.” 

Sam just stared, in complete and total disbelief. 

“I’m sorry I couldn’t do more,” Cas said, staring at the back of his hands. Jody put a hand on his shoulder. 

“It’s okay, Cas,” Sam said, feeling far away.

“He called me, from the hospital. Donna and Claire are working on it now, and I’ve got the police alerted too. Cas and I have been doing research from here, mostly. We left once or twice to check out leads.”

“And you’ve got nothing?” 

“No,” Cas said, practically spitting the word in frustration. “I called Rowena, and she attempted a scrying spell for them but the best she could do was tell us they were still in the country. Wherever they are, it’s heavily warded. Heavily enough that I can’t hear it if they’ve been praying to me.”

“Basically everyone we know is on the lookout,” Jody said. “We’ll find them, Sam. I know we will.” 

Sam looked between Jody and Cas, knowing that the look on his face was equally as stricken, and tried to find a spark of hope to cling to.

He may as well have been trying to find an ocean in the desert.

\----------

Jack was screaming again. Dean could hear it through the walls. He ignored it- wasn’t like there was anything he could do. They had him locked down on a table, pumped so full of the good stuff he couldn’t see. He didn’t know what they gave him, just that it hurt, hurt, _hurt_. And they’d stand there and take notes. Meticulous notes, good notes, like he bet Sammy took in college. 

He could feel himself talking, too. Long conversations with Sam and Cas, sometimes Jack, sometimes Bobby and Mom and Dad and long dead friends. 

Most of the time he just screamed. 

The good thing about the drugs though was that they always gave a buzz. So even if it burned its way right into his brain, made him so dizzy he vomited up blood and chunks of something not normal for vomit, or that he looked at his legs once and thought they looked a lot skinnier, or that he was pretty sure they’d shaved his head and attached those electric node thingies to it. That they wouldn’t let him sleep, leaving the lights dimmed and the temperature perfect but shocking him or hitting him or spraying him with freezing water when he got close. Maybe all that was okay because he couldn't really feel it. Kinda like he wasn't really here. 

Dean was so goddamn tired. 

Sometimes he laughed, sometimes he cried. Sometimes he was back in Cold Oak, screaming into the night holding Sam’s dead body. Sometimes he was back in Hell, screaming as Alastair ripped his skin off. 

Huh. Maybe it wasn’t the drugs. Maybe it was just him. 

Maybe Dean Winchester had finally gone off the rails for good. 

He asked Sam and Cas what they thought about that, and the only answer he got was an electric shock and Jack’s screaming through the walls. 

\--------

Sam tapped away at his laptop, scouring the internet for any mention of people matching Dean and Jack’s descriptions. Jody was on the phone with Donna, checking in from their side of things, and Cas was working on a location spell he’d wrung out of Sergei with some very creative death threats. 

They were getting nowhere. And Sam’s headache was getting worse. He’d caught Cas’s concerned glances, but he shrugged off every offer Cas made to heal him. What was the point? Cas was wrung out as it was, and they’d need every ounce of healing power he had when they found Dean and Jack. Just in case. 

Patience and Alex came back in the front door, looking dejected. They’d gone to Alex’s hospital to scour the medical database for John Does that could be Dean and Jack. No such luck, just like every day before that. While Sam had been fighting off whatever drug they’d given him. 

A drug Dean hadn’t gotten hospital care for. Jack might be strong enough to fight it, but if they had his powers locked down… Sam dropped his head into his hands, digging his palms into his eyelids. 

“Package on the porch, Jody,” Patience said, carrying it into the kitchen and placing it on the island. 

Jody pulled the phone back from her ear, covering the receiver with her hand. “Open it up for me, okay?” At Patience’s nod, Jody lifted the phone back up and kept talking to Donna. 

They had anxious silence for another minute, and then Patience screamed. 

Everyone rushed over, and Sam felt his breath catch at the contents of the box. Inside it lay a finger, blood dried around the base, and a bundle of tawny gold feathers. Sam thought he might be sick. 

Cas was looking green around the gills, too, but he was staring at the feathers with a look of such pure _fury_ that it nearly made Sam stumble back. 

“Are those... “ Jody’s voice trailed off. 

“Yes,” Cas all but growled. “Yes, they are. And I’m going to burn whoever did this to _ash_ and send them straight to Hell.” 

Alex moved to push the box closed, but Sam caught her hand, his eye catching on something underneath the finger. Dean’s finger. 

_Dear god._

It was a piece of paper. A piece of paper with an address, and a message. 

_Come get what’s left, if you want it. We got what we needed. You’ll be seeing us again soon._

“What the hell does that mean?” Jody asked. 

“I don’t know. But we have something, and we have to go get them,” Sam said. 

“I’ll start the car. You get the GPS.” And Cas was gone, already out the door with every fibre of his being vibrating with wrath. It was times like these Sam remembered how fortunate he was to be on Cas’s good side. 

“Okay,” he affirmed. “Let’s go.”

\----------

Dean was talking again. Jack could hear it through the walls. Not loud enough to make out words, but loud enough that Jack knew he was doing it. At least he knew Dean was still alive. 

Jack was strung up by his wrists from heavy, warded chains. His toes barely grazed the floor, and he was sure his wrists were broken by now. The metal cut, too, and so there were dried rivulets of blood trailing down his arms. He was fairly sure his fingers were frozen, since he couldn’t move them and it was cold in the room. 

They’d taken his shirt, and at first Jack had struggled when they put more cold metal on his back, but then something had _shifted_ and his wings were there. Really, physically, there. And the extra weight had been what snapped his wrists. 

It got worse, because at that point Jack was still struggling, even through the haze of whatever they’d injected. There were so many needles… all over him, there were needles. In his neck, taking little bits of grace, all over his body, taking blood, and a few in his brain that they were disappointed didn’t make him talk in Enochian. 

But his wings… they ran their hands all over them, first. And it felt so _wrong_. He tried to yell for them to stop, but then he got slapped across the face hard enough that he nearly bit his tongue off. And then they ripped his feathers out, and Jack couldn’t stop screaming. 

Now, they were gone. He didn’t know how long it had been, with hands and needles and knives all over him, taking bits of everything. His wrists were numb. His back ached. His wings screamed with agony, bringing tears to his eyes every time he shifted even a little bit. He dripped blood from a million needle marks on his torso, and more than anything he wanted to be home. 

He wanted to play board games with Cas and drink tea with Sam and watch movies with Dean. He wanted to curl up in his warm bed and sleep, in his room where Sam was right next door and Cas was always just a call away. 

He wanted his mother. He longed for that feeling of love he remembered from being in her womb, of the total safety and contentment he’d felt when he was with her and Castiel. 

He was so tired. He gave in to the pull of sleep, not caring whether he’d wake up. At least the pain would be gone. 

\----------

Castiel parked the car and threw open the door, fury and fear tearing through him. He and Sam had barely spoken on the way here, both too consumed with horror at the contents of the box. They’d brought it, hoping that Cas could reattach Dean’s finger. Assuming that Dean and Jack were here, and it wasn’t a ploy or a plot or a red herring. 

With a nod to each other, they moved into the warehouse. Jody followed behind them, silent. 

It was empty. Apparently, whoever wrote the message had left. Which meant Castiel would have to hunt them down and kill them at a later date. Right now, his priority was his family. 

They found Dean first, and he looked- well. Awful would be a terrible understatement. Dean was bloodied and emaciated, with dark bags under his eyes and patches of hair missing, electric nodes in its place over burned scalp. Sam immediately dropped to his knees beside his brother, trying to get any kind of response. There wasn’t one. Cas wordlessly took the box from Jody and moved to heal Dean’s finger as Jody called for an ambulance. Cas knew just from looking that he didn’t have the strength to heal the rest of this himself. 

Dean gasped awake, immediately falling into a coughing fit. 

“Dean! Hey, Dean, it’s okay. I’m here.” Sam shifted into Dean’s field of vision, wearing a watery farce of a smile. 

“Hey, Sammy. Do you hear that? Jack stopped screaming. I hope that’s a good thing. Where’d the doctors go, d’y’know? I hope they give me more of the buzzy stuff, because I think my brain is melting.” Dean smiled as he spoke, blood dribbling from his nose. Sam’s face pinched, and Cas’s heart clenched. He wished there was more he could do.

Jack. He had to find Jack. 

Knowing Sam had Dean, Cas pushed further into the warehouse. He found a second room down the hall and opened the door, the sight inside pulling the ground out from under him. 

Jack, unconscious and beaten, suspended from sigiled chains locking purple and swollen wrists into place. Jack’s wings were still manifested, and the patches of missing feathers made Cas want to _kill_ whoever had dared to touch his child. Instead he ran forward, yanking the chains out of the ceiling and gently breaking the metal off of Jack’s wrists. 

Cas caught Jack as he slumped forward, clammy skin coming into contact with Cas’s hands. Jack blinked, registering the touch. 

“No- stop, please. Whatever you want, I’ll do it- just- stop, let me down please, please, stop…”

“Jack, it’s me. It’s Castiel. You’re safe.” 

Cas maneuvered them down to the floor, trying to find a way to push Jack’s wings back to their dimension. 

A long moment later, Jack let out a shaky breath, maybe a sob, where his face was pressed into Cas’s shoulder. 

“It hurts, Cas.” 

“I know,” Cas whispered, cupping the back of Jack’s head gently with one of his hands. “I’m going to try and put your wings back, alright? It should be over quickly.” 

He waited until Jack nodded, and then pulled off whatever heinous devices they’d been using to keep his wings in this plane. Once they were gone Jack sagged against Cas, and Cas could wrap his arms around the boy fully. He only wished his wings were in good enough shape to wrap around him too. 

Cas pressed his fingers to Jack’s forehead, trying to heal him. As expected, it didn’t work. So Cas helped him up, wrapped him up in Cas’s own coat, and led him out to the ambulance where Sam and Jody were waiting.

\----------

Dean woke up with a splitting headache and a million questions. He was in a hospital room, hooked up to a gazillion humming machines. He didn’t remember how he got here. 

Sitting at his bedside was Sam, with a trench-coat clad Jack snoozing on his shoulder. Sam was passed out too, with his head resting gently on top of Jack’s. Dean swiveled his head the other way to see Cas staring out the window. 

“Cas?” Dean rasped. His friend jumped up, his exclamation of “Dean!” loud enough to wake Sam and Jack. Cas walked over to sit down next to them, and the three musketeers leaned over, asking a million questions about how he was feeling. Sam looked like shit, but he was at least smiling a little bit. 

“I’m fine, I’m fine,” he said. “I think. Does somebody want to tell me what happened?” 

And it was a hell of a story. A bit of a mess, with a lot of loose ends, but a story nonetheless. And with his family all here in one place? He really couldn’t care less.

**Notes for the Chapter:**

> And we're done! Thank you guys for sticking with me on this thing! I've never actually finished any kind of long-term project like this before, and it was really fun. You guys are the best, and your comments genuinely make my day. And I bet there were a few readers lurking (since that's how I read, lol) and I appreciate y'all too! 
> 
> I have a few multi-chapter fic ideas in the works, so stay tuned for those if you liked this! And I'd love any thoughts you have on this chapter or the story as a whole. Thanks again!


End file.
